Title: Dutchess County Villas | Expedia.ca [Dutchess County Hotels](https://expedia.ca/Destinations-In-Dutchess-County.d553248635083914455.Hotel-Destinations)[Vacation Rentals in Dutchess County](https://expedia.ca/Destinations-In-Dutchess-County.d553248635083914455.Vacation-Rental-Destinations)[Dutchess County Car Rentals](https://expedia.ca/Destinations-In-Dutchess-County.d553248635083914455.Car-Rental-Destinations)[Dutchess County Vacations](https://expedia.ca/Dutchess-County.d553248635083914455.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/6127069/a5f9e570-f4d7-4782-9239-15aa943a29e3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6127069/a5f9e570-f4d7-4782-9239-15aa943a29e3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635083914455&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=553248635083914455&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jul 3 - Jul 5](https://www.expedia.ca/Hotel-Search?regionId=553248635083914455&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 31 - Aug 2](https://www.expedia.ca/Hotel-Search?regionId=553248635083914455&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Dutchess County ![](https://images.trvl-media.com/place/6056317/3d0b867b-2959-4515-978a-1c7785c0358a.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Poughkeepsie [](https://expedia.ca/Poughkeepsie-Villas.d6056317-aaVillas.Travel-Guide-Accommodation) ![](https://images.trvl-media.com/place/55927/3e76cd2b-20c9-48e9-9d2e-169e78b8f5c3.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Rhinebeck [](https://expedia.ca/Rhinebeck-Villas.d55927-aaVillas.Travel-Guide-Accommodation) ![B06FJJ Business district of Beacon New York Hudson Valley. Image shot 2008. Exact date unknown.](https://images.trvl-media.com/place/6173904/55c8df06-2cd9-4a33-bcb7-e73edea8924b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Beacon [](https://expedia.ca/Beacon-Villas.d6173904-aaVillas.Travel-Guide-Accommodation) ![Beacon, NY - USA - Nov. 29, 2020: Landscape view of the iconic Beacon Falls on the Fishkill creek, located off of Main Street in Beacon.](https://images.trvl-media.com/place/55704/6591ab52-4b44-401d-81bb-f4f88568b42a.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Fishkill [](https://expedia.ca/Fishkill-Villas.d55704-aaVillas.Travel-Guide-Accommodation) ![Serpentine Gallery in Hyde Park](https://images.trvl-media.com/place/117834/533275d8-b9b2-4721-a987-03247f6d48fd.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Hyde Park [](https://expedia.ca/Hyde-Park-Villas.d117834-aaVillas.Travel-Guide-Accommodation) ![Panoramic view from Bear Mountain](https://images.trvl-media.com/place/56028/2be41f76-ad2a-4932-8fe8-129e205f022d.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Wappingers Falls [](https://expedia.ca/Wappingers-Falls-Villas.d56028-aaVillas.Travel-Guide-Accommodation) ## Our top choices for Dutchess County villas ![Exterior](https://images.trvl-media.com/lodging/119000000/118010000/118005500/118005460/aafc7e1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/119000000/118010000/118005500/118005460/0f0021eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118010000/118005500/118005460/5a0b1e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118010000/118005500/118005460/44f43ec4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space [](https://www.expedia.ca/Monroe-Hotels-7BR-Monroe-Getaway-Pool.h118005460.Hotel-Information) Monroe 6.8/10 (5 reviews) "It was a great home with lots of space indoor and outside. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yogita R. [](https://www.expedia.ca/Monroe-Hotels-7BR-Monroe-Getaway-Pool.h118005460.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83820000/83816500/83816417/e1bb5765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83820000/83816500/83816417/0483960f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/84000000/83820000/83816500/83816417/d1607b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83820000/83816500/83816417/017494e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Scenic Mansion With Breathtaking View [](https://www.expedia.ca/Highland-Hotels-The-Scenic-Mansion-With-Breathtaking-View.h83816417.Hotel-Information) Highland 8.8/10 Excellent (18 reviews) "This was a extended work visit, and the property was perfect for us and the host was very accommodating whenever needed. I can see a wedding, reunion or a quiet getaway for a large family at this location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gordon V. [](https://www.expedia.ca/Highland-Hotels-The-Scenic-Mansion-With-Breathtaking-View.h83816417.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218543/61d33629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218543/e8c36ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218543/ebde2567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218543/c0a34199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Mountain Villa [](https://www.expedia.ca/Round-Top-Hotels-Beautiful-Mountain-Villa.h93218543.Hotel-Information) Round Top 9.0/10 Wonderful (6 reviews) "The hosts were great. They were very accommodating. we had a 50th birthday party and their property was perfect for it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie G. [](https://www.expedia.ca/Round-Top-Hotels-Beautiful-Mountain-Villa.h93218543.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/abd47b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/84afbd11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/a09b00a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/31f65901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT [](https://www.expedia.ca/Brewster-Hotels-Upstate-Historical-Artist-Villa-W-Firepit.h101878310.Hotel-Information) Brewster 9.2/10 Wonderful (7 reviews) "Property was exactly what we were looking for with a group as large as ours (14 people). Plenty of indoor and outdoor space. Great kitchen as well (cooked all of our meals in the house for the whole group)." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric L. [](https://www.expedia.ca/Brewster-Hotels-Upstate-Historical-Artist-Villa-W-Firepit.h101878310.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91380000/91377600/91377526/b23361ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/92000000/91380000/91377600/91377526/df4d113b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/92000000/91380000/91377600/91377526/c69b98b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91380000/91377600/91377526/84ed658e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Mountain Getaway, Fire Pit,Arcade, Hot Tub, Near Lake Minnewaska [](https://www.expedia.ca/Kerhonkson-Hotels-Happy-Minnewaska-Deluxe-Villa-PoolArcadeHot-Tub.h91377526.Hotel-Information) Kerhonkson 10/10 Exceptional (3 reviews) "This property was adorable. We loved the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica B. [](https://www.expedia.ca/Kerhonkson-Hotels-Happy-Minnewaska-Deluxe-Villa-PoolArcadeHot-Tub.h91377526.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/47000000/46990000/46987600/46987580/dd69f81a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, Netflix](https://images.trvl-media.com/lodging/47000000/46990000/46987600/46987580/0fd4290e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/47000000/46990000/46987600/46987580/d7ad98b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/47000000/46990000/46987600/46987580/2f0d705e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enchanting Tannersville Mansion W Erov 4 Groups & Families Hot-Tub 5Bds+3.5Bath [](https://www.expedia.ca/Tannersville-Hotels-Enchanting-Tannersville-Mansion-W-Erov-4-Groups-Families-Hot-Tub-5Bds35Bath.h46987580.Hotel-Information) Tannersville 9.2/10 Wonderful (14 reviews) "Great location, good communication with owner. No complaints." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hiram D. [](https://www.expedia.ca/Tannersville-Hotels-Enchanting-Tannersville-Mansion-W-Erov-4-Groups-Families-Hot-Tub-5Bds35Bath.h46987580.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83560000/83558200/83558149/w2018h1342x0y0-fd6b04a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/84000000/83560000/83558200/83558149/0a2ba355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![45-inch Smart TV with cable channels, TV, fireplace](https://images.trvl-media.com/lodging/84000000/83560000/83558200/83558149/1b83f32c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design House | Private kitchen](https://images.trvl-media.com/lodging/84000000/83560000/83558200/83558149/w1796h1338x2y0-ca92adbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dome House Retreat [](https://www.expedia.ca/New-Paltz-Hotels-Dome-House-Retreat.h83558149.Hotel-Information) New Paltz [](https://www.expedia.ca/New-Paltz-Hotels-Dome-House-Retreat.h83558149.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102340000/102333300/102333283/w1024h554x0y64-8a57e32d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/103000000/102340000/102333300/102333283/w920h683x52y0-f1a32102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/103000000/102340000/102333300/102333283/w923h683x50y0-a76ad0dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/103000000/102340000/102333300/102333283/w1024h616x0y33-654daed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CHALET with INDOOR POOLHOUSE base of HUNTER mountain [](https://www.expedia.ca/Hunter-Hotels-Log-Cabin-With-INDOOR-POOL-Foot-Of-Hunter-Mountain.h102333283.Hotel-Information) Lanesville 9.6/10 Exceptional (8 reviews) "We had 45 birthday with 6 couples and it was perfect.It is a great place for a large group. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris B. [](https://www.expedia.ca/Hunter-Hotels-Log-Cabin-With-INDOOR-POOL-Foot-Of-Hunter-Mountain.h102333283.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/22000000/21480000/21473600/21473546/92b05735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/22000000/21480000/21473600/21473546/65ccdc99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21480000/21473600/21473546/2c9c2117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/22000000/21480000/21473600/21473546/e35c654a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC [](https://www.expedia.ca/Harriman-Hotels-Stunning-Mansion.h21473546.Hotel-Information) Harriman 10/10 Exceptional (81 reviews) "Our stay was very pleasant and the host was very responsive and made sure an issue was quickly resolved. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elan N. [](https://www.expedia.ca/Harriman-Hotels-Stunning-Mansion.h21473546.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/23000000/22240000/22235000/22234975/e488de7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22240000/22235000/22234975/3c3e2fac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/23000000/22240000/22235000/22234975/5960a531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video-game console, DVD player](https://images.trvl-media.com/lodging/23000000/22240000/22235000/22234975/27ae15a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Luxury 5BR3BTh Woodstock Secret Retreat Near all Ski MT Heated Pool& Hot Tub [](https://www.expedia.ca/Woodstock-Hotels-New-Luxury-5BR-Woodstock-Secret-Retreat-Near-All-Ski-MT-Heated-Pool-Hot-Tub.h22234975.Hotel-Information) Woodstock 9.6/10 Exceptional (28 reviews) "Great backyard, pool, etc. Spacious, comfortable home. Needs updating. Unfortunately owner video records open areas in home. Illegal and invasion of privacy. He also wants a signed agreement with him, not VRBO after payment was put down with outrageous stipulations like $1000 fine if pool cover is left off. Again, illegal." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sally L. [](https://www.expedia.ca/Woodstock-Hotels-New-Luxury-5BR-Woodstock-Secret-Retreat-Near-All-Ski-MT-Heated-Pool-Hot-Tub.h22234975.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113610000/113603200/113603125/7909688d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/114000000/113610000/113603200/113603125/b96009d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![9 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113610000/113603200/113603125/f2f540d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113610000/113603200/113603125/e8ace80f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Retreat w/ Pool, Hot Tub & Game Room [](https://www.expedia.ca/Stony-Point-Hotels-Spacious-Retreat-W-Pool.h113603125.Hotel-Information) Stony Point 4.0/10 (1 review) "The house itself was fine but the pool was unusable and not maintained. We were frequently promised it would be fixed each day but there was no maintenance done. Even going through support, there was no attempt to make things right and we were unable to use the pool during a hot summer weekend. (There aren't even any pool towels for use)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin L. [](https://www.expedia.ca/Stony-Point-Hotels-Spacious-Retreat-W-Pool.h113603125.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118870000/118869300/118869279/773df58e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/119000000/118870000/118869300/118869279/a657681a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118870000/118869300/118869279/62684886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118870000/118869300/118869279/8dbe65da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge [](https://www.expedia.ca/Stony-Point-Hotels-Luxury-10BR-Escape-W-Pool.h118869279.Hotel-Information) Stony Point [](https://www.expedia.ca/Stony-Point-Hotels-Luxury-10BR-Escape-W-Pool.h118869279.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33580000/33571600/33571555/820530ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33580000/33571600/33571555/ef25aae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33580000/33571600/33571555/e48d7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33580000/33571600/33571555/faf6e3a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captivating Artisan Built Home With Spectacular Water Views [](https://www.expedia.ca/Falls-Village-Hotels-Captivating-Artisan-Built-Home-With-Spectacular-Water-Views.h33571555.Hotel-Information) Falls Village 10/10 Exceptional (115 reviews) "Lovely property! The cottage is in an ideal location amd had everything we needed. The house is decorated beautifully and in great shape. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DANA C. [](https://www.expedia.ca/Falls-Village-Hotels-Captivating-Artisan-Built-Home-With-Spectacular-Water-Views.h33571555.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/126000000/125310000/125300500/125300416/9991e871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125310000/125300500/125300416/3fa6ebee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125310000/125300500/125300416/73b99a00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/126000000/125310000/125300500/125300416/d53ac044.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand 10BR Retreat w/Pool & Hot Tub [](https://www.expedia.ca/Chester-Hotels-Grand-9BR-Retreat-WPool-Hot-Tub.h125300416.Hotel-Information) Chester 2.0/10 (1 review) "All our children were allergic to hot water .The water was not clean .The landlord should have cleaned it with chlorine ,but he didn’t." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gulshoda K. [](https://www.expedia.ca/Chester-Hotels-Grand-9BR-Retreat-WPool-Hot-Tub.h125300416.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/83000000/82800000/82793700/82793654/5469e87c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/83000000/82800000/82793700/82793654/c601789a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82800000/82793700/82793654/00f6e342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/83000000/82800000/82793700/82793654/c84d9c52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rhinebrook Estate - 8 Bed/8Bath (Sleeps 20) [](https://www.expedia.ca/Hyde-Park-Hotels-Rhinebrook-Estate-8-Bed8Bath.h82793654.Hotel-Information) Hyde Park 9.6/10 Exceptional (19 reviews) "This breathtaking mansion exceeded all expectations. It was in pristine condition and so so clean. Lots of space for a dinner party and playing board games. The kitchen was spacious and convenient to cook in with a huge refrigerator, 2 sinks, and 2 dish washers. Each bedroom was very spacious with most having their own bathroom. The cherry on top was the yoga room, sauna room, and outdoor hot tub. Was the best house stay I have ever had.." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alina D. [](https://www.expedia.ca/Hyde-Park-Hotels-Rhinebrook-Estate-8-Bed8Bath.h82793654.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107830000/107826200/107826191/3a796385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107830000/107826200/107826191/9d428ffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107830000/107826200/107826191/caba16b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, offices](https://images.trvl-media.com/lodging/108000000/107830000/107826200/107826191/a503abb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Group Retreat w. Backyard, BBQ, Gym, Games & More! [](https://www.expedia.ca/Stony-Point-Hotels-5-Bdrm-Luxury-Near-West-Point-With-Gym.h107826191.Hotel-Information) Stony Point 9.6/10 Exceptional (5 reviews) "Great place with ample room for our large party of 15 to celebrate the holidays! Hosts were very communicative and helpful. Only opportunity for improvement would be to increase kitchen stock items (plates glasses bowls utensils etc) and add another bathroom. Thanks for a great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Family T. [](https://www.expedia.ca/Stony-Point-Hotels-5-Bdrm-Luxury-Near-West-Point-With-Gym.h107826191.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111170000/111163100/111163059/25b9c086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books](https://images.trvl-media.com/lodging/112000000/111170000/111163100/111163059/884bbe55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111170000/111163100/111163059/f2da2586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books](https://images.trvl-media.com/lodging/112000000/111170000/111163100/111163059/2de7a6e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game [](https://www.expedia.ca/Hudson-Hotels-Mountain-View-Retreat-Heart-Of-Hudson-With-Decks.h111163059.Hotel-Information) Hudson 9.6/10 Exceptional (14 reviews) "Love the place game room and all rooms are big bathrooms are perfect " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James [](https://www.expedia.ca/Hudson-Hotels-Mountain-View-Retreat-Heart-Of-Hudson-With-Decks.h111163059.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83450000/83440200/83440144/d8a9f369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83450000/83440200/83440144/f88b91a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83450000/83440200/83440144/2c9cf8bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/84000000/83450000/83440200/83440144/8d01e00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Retreat Villa: Theater, Yoga Studio, Group Spaces | Dream House in the Gunks [](https://www.expedia.ca/Kerhonkson-Hotels-Villa-Retreat-In-Nature-With-Private-Yoga-Studio.h83440144.Hotel-Information) Kerhonkson 10/10 Exceptional (9 reviews) "This property was perfect for my group of 11 friends. Great amenities and great location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lily M. [](https://www.expedia.ca/Kerhonkson-Hotels-Villa-Retreat-In-Nature-With-Private-Yoga-Studio.h83440144.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83650000/83646900/83646889/w1024h682x0y1-5f483e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83650000/83646900/83646889/5ff874d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/84000000/83650000/83646900/83646889/2424ced0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/84000000/83650000/83646900/83646889/w1024h682x0y1-1f21bb01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard [](https://www.expedia.ca/Chester-Hotels-Magnificent-Villa.h83646889.Hotel-Information) Chester 9.6/10 Exceptional (13 reviews) "Lovely home and property. Lots of space, fit everyone and then some! Ample bedrooms with lots of bed combinations to choose from. Had everything you could need, bathrooms stocked with toiletries incase you forgot anything. The game room downstairs was a huge hit as well. Would definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carley N. [](https://www.expedia.ca/Chester-Hotels-Magnificent-Villa.h83646889.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107030000/107027000/107026903/9bad3f30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107030000/107027000/107026903/w1439h959x1y1-0482d52c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/108000000/107030000/107027000/107026903/w1440h959x0y1-63fe01ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/108000000/107030000/107027000/107026903/05924300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY. [](https://www.expedia.ca/Monroe-Hotels-Spacious-Beautiful-5-Bedroom-Mediterranean-Villa-In-Monroe.h107026903.Hotel-Information) Monroe 9.0/10 Wonderful (11 reviews) "Beautiful home!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley T. [](https://www.expedia.ca/Monroe-Hotels-Spacious-Beautiful-5-Bedroom-Mediterranean-Villa-In-Monroe.h107026903.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-04-21&endDate=2026-04-22®ionId=553248635083914455&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Dutchess+County%2C+New+York%2C+United+States+of+America®ionId=553248635083914455&latLong=41.778439%2C-73.747787&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Dutchess+County%2C+New+York%2C+United+States+of+America®ionId=553248635083914455&latLong=41.778439%2C-73.747787&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=COTTAGE) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Dutchess+County%2C+New+York%2C+United+States+of+America®ionId=553248635083914455&latLong=41.778439%2C-73.747787&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CHALET) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Dutchess+County%2C+New+York%2C+United+States+of+America®ionId=553248635083914455&latLong=41.778439%2C-73.747787&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Dutchess+County%2C+New+York%2C+United+States+of+America®ionId=553248635083914455&latLong=41.778439%2C-73.747787&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Dutchess+County%2C+New+York%2C+United+States+of+America®ionId=553248635083914455&latLong=41.778439%2C-73.747787&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Dutchess+County%2C+New+York%2C+United+States+of+America®ionId=553248635083914455&latLong=41.778439%2C-73.747787&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Dutchess+County%2C+New+York%2C+United+States+of+America®ionId=553248635083914455&latLong=41.778439%2C-73.747787&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VILLA) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Dutchess+County%2C+New+York%2C+United+States+of+America®ionId=553248635083914455&latLong=41.778439%2C-73.747787&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=HOUSE_BOAT) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDutchess-County-Villas.d553248635083914455-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDutchess-County-Villas.d553248635083914455-aaVillas.Travel-Guide-Accommodation) ## Top Dutchess County Hotel Reviews ![Beekman Arms and Delamater Inn](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/ab673905_y.jpg) ### Beekman Arms and Delamater Inn 10/10 Excellent "Classic historic hotel- loved the cozy lobby with fireplace and the morning coffee, and the taproom. TV in the room was a little wonky but weren’t really there to watch TV. " [](https://expedia.ca/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![Home2 Suites By Hilton Poughkeepsie](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/7472348e_y.jpg) ### Home2 Suites By Hilton Poughkeepsie 10/10 Excellent "very nice hotel. Large spacious rooms." [](https://expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/ee108dad_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "Great location " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Best Western Danbury/Bethel](https://images.trvl-media.com/lodging/1000000/10000/4900/4841/b09513bc_y.jpg) ### Best Western Danbury/Bethel 8/10 Good "Hotel was nice, breakfast was rather good, but bed was easy to hard for my liking. " [](https://expedia.ca/Danbury-Hotels-Best-Western-DanburyBethel.h4841.Hotel-Information) ![Best Western Fishkill Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/12500/12443/847efacf_y.jpg) ### Best Western Fishkill Inn & Suites 10/10 Excellent "I like this hole so much! It is very spacious and comes with a complete kitchen. It is close to West Point Military Academy and the outlet. There is free parking available and dogs can be accommodated. It is truly perfect. " [](https://expedia.ca/Fishkill-Hotels-Best-Western-Fishkill-Inn-Suites.h12443.Hotel-Information) ![HYATT house Fishkill/Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/w3836h2558x4y3-858cbdd6_y.jpg) ### HYATT house Fishkill/Poughkeepsie 10/10 Excellent "Staff was great, I have a special needs son they were very accommodating. Definitely will be returning 🔥🔥🤘" [](https://expedia.ca/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.Hotel-Information) ![Hyatt Place Poughkeepsie / Hudson Valley](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd_y.jpg) ### Hyatt Place Poughkeepsie / Hudson Valley 10/10 Excellent "Friendly staff all-around. Great breakfast, clean premises and room. Very quiet. Would stay again. " [](https://expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information) ![Spark by Hilton Fishkill](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f_y.jpg) ### Spark by Hilton Fishkill 10/10 Excellent "Room was clean but very minimalist. Not much furniture. No refrigerator. Offered 24 hour coffee and tea. Daily free newspaper. Nice breakfast. Friendly staff." [](https://expedia.ca/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "This was my first time staying here and the service was excellent will return soon " [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ## Find out more about Dutchess County ## Dutchess County Villas information | Number of reviews | 335 | | ----------------- | --------- | | Accommodation | 33 Villas | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Millbrook ](https://www.expedia.ca/5Star-Millbrook-Hotels.s50-0-d6051715.Travel-Guide-Filter-Hotels) - [Bangall Hotels ](https://www.expedia.ca/Bangall-Hotels.d3000447992.Travel-Guide-Hotels) - [Hotels & Resorts for Couples in Clinton Corners ](https://www.expedia.ca/Clinton-Corners-Hotels-Couples-Resorts-Hotels.0-0-d6173896-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - 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