Title: Pound Ridge Vacation Home Rentals from CA $268: Search Top Private Vacation Homes for Rent | Expedia.ca [Pound Ridge Travel Guide](https://expedia.ca/Pound-Ridge.dx3000449463)[Hotels in Pound Ridge](https://expedia.ca/Pound-Ridge-Hotels.d3000449463.Travel-Guide-Hotels)[Vacation Rentals in Pound Ridge](https://expedia.ca/Pound-Ridge-Vacation-Rentals.d3000449463.Travel-Guide-VacationRentals)[Pound Ridge Car Rentals](https://expedia.ca/Car-Rentals-In-Pound-Ridge.d3000449463.Car-Rental-Guide)[Pound Ridge Vacation Packages](https://expedia.ca/Pound-Ridge.d3000449463.Destination-Travel-Guides) ![The Spring bloom creates a colorful scene.](https://images.trvl-media.com/place/3000449463/a0fa9f4e-2071-432b-bc85-3dd175484ad9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Pound Ridge Vacation Rentals - ![](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 Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000449463&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000449463&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=3000449463&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=3000449463&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pound Ridge vacation homes ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/1366870a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/6a37565c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/163d5bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111690000/111683300/111683284/218721ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House, [](https://www.expedia.ca/Charming.h111683284.Hotel-Information) Shelton 9.0/10 Wonderful (2) "The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex C. CA $165 CA $268 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Charming.h111683284.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/bdac6c18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/fd769a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/4388309b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/3c5edeb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Country outside the city " 3 bedrooms 2 full bathrooms [](https://www.expedia.ca/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information) Holmes 9.6/10 Exceptional (4) "Great house! We had a fantastic weekend!! Thank you so much " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) pamela w. CA $241 CA $747 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95900000/95891300/95891227/bcb11e3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/96000000/95900000/95891300/95891227/5eb9279b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95900000/95891300/95891227/d50b7da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95900000/95891300/95891227/343b9d7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marine Theme - 4 BR - Backyard - Fire pit [](https://www.expedia.ca/Bridgeport-Hotels-Marine-Theme-4-BR-Backyard-Fire-Pit.h95891227.Hotel-Information) North End 9.8/10 Exceptional (8) "We were in town for a short stay and everything was very nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin B. CA $197 CA $543 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Bridgeport-Hotels-Marine-Theme-4-BR-Backyard-Fire-Pit.h95891227.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/7ce63cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/c1311c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/71684fe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/32fb7c3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock. [](https://www.expedia.ca/Greenwich-Hotels-2-Bedroom-And-1-Full-Bath-In-Lakeside-Home-With-Private-Dock.h114606188.Hotel-Information) Greenwich 9.6/10 Exceptional (23) "The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victoria R. CA $177 CA $367 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Greenwich-Hotels-2-Bedroom-And-1-Full-Bath-In-Lakeside-Home-With-Private-Dock.h114606188.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/38809636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/8bc06f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/cfa82cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/07a03d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike. [](https://www.expedia.ca/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information) Carmel Hamlet 9.8/10 Exceptional (12) "We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah P. CA $229 CA $489 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/88000000/87230000/87226100/87226001/3a1df8f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87230000/87226100/87226001/001088a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/88000000/87230000/87226100/87226001/33d9009b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/88000000/87230000/87226100/87226001/2106b7f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centric property close to all the great things in the city [](https://www.expedia.ca/Bridgeport-Hotels-Golden-Colonial-Home-Family-Friendly.h87226001.Hotel-Information) Brooklawn - St. Vincent 7.2/10 Good (13) "This rental was great accommodation" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alma B. CA $217 CA $410 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Bridgeport-Hotels-Golden-Colonial-Home-Family-Friendly.h87226001.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/7e38644f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/f9f598e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/23bd3ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/118900b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright Escape, Top-Rated Design, Fire pit, Near Beach [](https://www.expedia.ca/Fairfield-Hotels-Renovated-Retreat-WFire-Pit.h110275967.Hotel-Information) Fairfield 10/10 Exceptional (11) "Convenient to everything. Lovely place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tami S. CA $267 CA $690 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Fairfield-Hotels-Renovated-Retreat-WFire-Pit.h110275967.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/3138ca99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/ac1bba42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/2730f6d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/bdaff4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi [](https://www.expedia.ca/Stamford-Hotels-Charming-2-Bedroom-House-In-Fabulous-Stamford-With-AC.h112364813.Hotel-Information) Waterside 9.8/10 Exceptional (9) "Lovely little home in Stamford." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pat A. CA $217 CA $453 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Stamford-Hotels-Charming-2-Bedroom-House-In-Fabulous-Stamford-With-AC.h112364813.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/4a974bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/d0c4b7c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/9094790c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/2af67e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC [](https://www.expedia.ca/Fairfield-Hotels-Family-Friendly-Renovated.h96133224.Hotel-Information) Fairfield 10/10 Exceptional (22) "Great family home. Location is perfect, close to everything yet private and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret W. CA $258 CA $662 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Fairfield-Hotels-Family-Friendly-Renovated.h96133224.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/23242491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/341c737a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/f998235d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/e34b64d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake [](https://www.expedia.ca/New-Fairfield-Hotels-Peaceful-All-Season-Lake-Community-Home.h100167349.Hotel-Information) New Fairfield 10/10 Exceptional (16) "The house worked very well for our family holiday. Very clean, had everything we needed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Audrey P. CA $284 CA $715 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/New-Fairfield-Hotels-Peaceful-All-Season-Lake-Community-Home.h100167349.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/79be2bfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch Smart TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/be85176a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch Smart TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/7643b925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/72602a0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways! [](https://www.expedia.ca/Bridgeport-Hotels-Charming-Colonial-Retreat-Perfect-For-Family-Getaways.h112048293.Hotel-Information) North End 9.4/10 Exceptional (6) "This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) April R. CA $1,209 CA $2,186 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Bridgeport-Hotels-Charming-Colonial-Retreat-Perfect-For-Family-Getaways.h112048293.Hotel-Information) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101740000/101736200/101736107/ae2c7036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101740000/101736200/101736107/342451b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101740000/101736200/101736107/a17843ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/102000000/101740000/101736200/101736107/e3e3d768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The B&W Haven 5BR Home with yard theater + Office [](https://www.expedia.ca/Bridgeport-Hotels-The-BW-Haven-5BR-Home-With-Yard-Theater-Office.h101736107.Hotel-Information) Brooklawn - St. Vincent 9.4/10 Exceptional (8) "Host was very polite and communicated well throughout the stay. The property appears well maintained. There are window units but everyone was comfortable for the duration of our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George M. CA $394 CA $926 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Bridgeport-Hotels-The-BW-Haven-5BR-Home-With-Yard-Theater-Office.h101736107.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/6e17e1d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium House, Garden View | Living area](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/4b24f4d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/b499b2ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium House, Garden View | Living area](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/7eecbab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beechmont - Perfect for Family Retreat! [](https://www.expedia.ca/Bridgeport-Hotels-Beechmont.h119248411.Hotel-Information) North End CA $1,166 CA $1,823 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Bridgeport-Hotels-Beechmont.h119248411.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/13a12d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/6b5d7309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/4d74027f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/92000000/91020000/91013300/91013202/95e392e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern + Spacious 5BR/2BA Home, Renovated Backyard [](https://www.expedia.ca/Bridgeport-Hotels-Modern-Spacious-5BR2BA-Home.h91013202.Hotel-Information) West End - West Side 9.6/10 Exceptional (4) "Used for family weekend at SHU. Convenient location and plenty of space for the whole family! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurene S. CA $489 CA $1,065 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Bridgeport-Hotels-Modern-Spacious-5BR2BA-Home.h91013202.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114300000/114291600/114291600/0e6e3fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114300000/114291600/114291600/4c1237e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114300000/114291600/114291600/d2a199e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114300000/114291600/114291600/ec029251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna [](https://www.expedia.ca/Fairfield-Hotels-Luxury-Estate-W-Heated-Pool.h114291600.Hotel-Information) Fairfield 10/10 Exceptional (1) "The Host was welcoming and responsive to our inquiries!Our stay was wonderful! The property was spectacular and offered all the amenities we needed for a comfortable and enjoyable visit. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia B. CA $1,044 CA $2,547 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Fairfield-Hotels-Luxury-Estate-W-Heated-Pool.h114291600.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/32d0bc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/d9fd7f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/e5a3641b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/3745699f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary Cozy Cottage [](https://www.expedia.ca/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information) Lake Peekskill 10/10 Exceptional (30) "Very clean comfortable quiet place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mauro C. CA $344 CA $622 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/119000000/118330000/118324400/118324337/b651961b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/119000000/118330000/118324400/118324337/36010145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118330000/118324400/118324337/1b77315b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118330000/118324400/118324337/8d39177e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Retreat | Heated Saltwater Pool | BBQ | Fire Pit [](https://www.expedia.ca/Redding-Hotels-Renovated-Retreat-Heated-Saltwater-Pool-BBQ.h118324337.Hotel-Information) Redding 10/10 Exceptional (2) "Beautiful house, very clean, spacious and a great host!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alejandro A. CA $317 CA $807 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Redding-Hotels-Renovated-Retreat-Heated-Saltwater-Pool-BBQ.h118324337.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/ef5e3737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/6d38d092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/34f76438.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/107000000/106570000/106560900/106560827/e3c3e5da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC [](https://www.expedia.ca/Norwalk-Hotels-Family-Friendly.h106560827.Hotel-Information) Historic District 10/10 Exceptional (8) "We were so pleased with the accommodations. The location is so quiet in a charming neighborhood. The home is well equipped with kitchen supplied and entertainment options. We were delighted to be able to barbecue. Claudia is very responsive and helpful." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) nawab k. CA $330 CA $765 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Norwalk-Hotels-Family-Friendly.h106560827.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95630000/95621700/95621659/5211a032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/96000000/95630000/95621700/95621659/6b4b9156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/96000000/95630000/95621700/95621659/220d7b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95630000/95621700/95621659/eaee0fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 45 Minutes from NYC, Entire House near Stamford Downtown, [](https://www.expedia.ca/Stamford-Hotels-45-Minutes-From-NYC.h95621659.Hotel-Information) Downtown Stamford 10/10 Exceptional (21) "Our hosts were very attentive and responsive with communications. The house is lovely, clean, well stocked and in a great location. We thoroughly enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan P. CA $255 CA $553 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Stamford-Hotels-45-Minutes-From-NYC.h95621659.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760929/adf16c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760929/412d20fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760929/c649c009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760929/1085fd12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright Stylish Chic 4BR 4BA Home Pet Friendly! [](https://www.expedia.ca/Stamford-Hotels-Bright-Stylish-Chic-4BR-4BA-Home-Pet-Friendly.h18760929.Hotel-Information) North Stamford 10/10 Exceptional (105) "Wonderful family home!Everything you need!Beautiful location!Great host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda T. CA $577 CA $1,265 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Stamford-Hotels-Bright-Stylish-Chic-4BR-4BA-Home-Pet-Friendly.h18760929.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=2025-12-26&endDate=2025-12-27®ionId=3000449463&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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%2FPound-Ridge-Private-Vacation-Homes.d3000449463-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPound-Ridge-Private-Vacation-Homes.d3000449463-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Pound Ridge Hotel Reviews ![Tarrytown House Estate](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg) ### Tarrytown House Estate 10/10 Excellent "I am a frequent guest here. Love it every time." [](https://expedia.ca/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![Baymont by Wyndham White Plains - Elmsford](https://images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg) ### Baymont by Wyndham White Plains - Elmsford 10/10 Excellent "The lady receptionist was efficient pleasant The room was comfortable and heating system efficient Breakfast was very good and simple Great deal for the price " [](https://expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ![HYATT house White Plains](https://images.trvl-media.com/lodging/1000000/430000/427300/427283/458cd7c2_y.jpg) ### HYATT house White Plains 10/10 Excellent "Great hotel" [](https://expedia.ca/White-Plains-Hotels-HYATT-House-White-Plains.h427283.Hotel-Information) ![Ardsley Acres Hotel Westchester](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166864/4b305bf7_y.jpg) ### Ardsley Acres Hotel Westchester 10/10 Excellent "Good place " [](https://expedia.ca/White-Plains-Hotels-Ardsley-Acres-Hotel-Westchester.h1166864.Hotel-Information) ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg) ### Sonesta White Plains Downtown 10/10 Excellent "Clean room. Courteous staff. " [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![West Gate Inn Nyack](https://images.trvl-media.com/lodging/6000000/5850000/5843400/5843352/393dcf26_y.jpg) ### West Gate Inn Nyack 10/10 Excellent "Greg and the whole staff have been so fantastic with my horrible situation. Definitely recommend staying there " [](https://expedia.ca/Nyack-Hotels-West-Gate-Inn-Nyack.h5843352.Hotel-Information) ![Courtyard by Marriott Yonkers Westchester County](https://images.trvl-media.com/lodging/18000000/17960000/17958000/17957993/33a84990_y.jpg) ### Courtyard by Marriott Yonkers Westchester County 10/10 Excellent "Spotless room, spotless common areas, nice bistro." [](https://expedia.ca/White-Plains-Hotels-Courtyard-By-Marriott-Yonkers-Westchester-County.h17957993.Hotel-Information) ![Hyatt Regency Greenwich](https://images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg) ### Hyatt Regency Greenwich 10/10 Excellent "Excellent Hotel, the room, the staff, the common areas, the bar, the coffee shop, everything about this hotel is great " [](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information) ![Amsterdam Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg) ### Amsterdam Hotel 10/10 Excellent "All was great" [](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.Hotel-Information) ## Find out more about Pound Ridge ## Pound Ridge Vacation Homes information | Number of reviews | 286 | | ----------------- | ------------------ | | Accommodation | 361 Vacation Homes | | Lowest Price | CA $268 | | Highest Price | CA $2,547 | ## Explore a world of travel with Expedia - 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