Title: Cutchogue Vacation Home Rentals from CA $364: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Cutchogue](https://expedia.ca/Cutchogue-Hotels.d183659.Travel-Guide-Hotels)[Vacation Rentals in Cutchogue](https://expedia.ca/Cutchogue-Vacation-Rentals.d183659.Travel-Guide-VacationRentals)[Cutchogue Car Rentals](https://expedia.ca/Car-Rentals-In-Cutchogue.d183659.Car-Rental-Guide)[Cutchogue Vacation Packages](https://expedia.ca/Cutchogue.d183659.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/dff376d916af97d7b1d400e631f0d46e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Adriana T # Cutchogue Vacation Rentals ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183659&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183659&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=183659&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=183659&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cutchogue Vacation Homes ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/7a209baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/b061fa88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/8f1986e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/d26d882e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sag Harbor Water View w Dock 1.5ml from town Bay Point CA $6,278 CA $8,917 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Water-View-W-Dock.h113439409.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/f6c15885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/b7d556ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/aeb85212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/d416d8d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5-bedroom house with water views and 2 houses from the bay. Sag Harbor CA $5,581 CA $8,949 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/c1c14546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/b0e8e3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/9a2f74fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/618fa7d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor Bridgehampton 9.6/10 Exceptional (15) "We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! " CA $231 CA $548 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Bridgehampton-Hotels-Cozy-Bungalow-Available-Nearby-Bridgehampton-And-Sag-Harbor.h105953994.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/b3f1fe2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/3368cbed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/98c458f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/441cf856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town Water Mill 10/10 Exceptional (6) "Highly recommend everything from start to finish went smoothly and it was a great experience!!" CA $4,186 CA $8,192 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/728215df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/a7476bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/38c1ca05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/ea540de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shoreline Oasis Clinton 9.2/10 Wonderful (7) "A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!" CA $250 CA $364 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Clinton-Hotels-Shoreline-Oasis.h113308197.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/f20bc122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8791fbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8ea39820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/00b024ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private beach on a fenced in property sunset views Hampton Bays 10/10 Exceptional (12) "We liked our stay there. Clean house, beautiful sunset as described. Close to the beach. Very nice stay." [](https://www.expedia.ca/Hampton-Bays-Hotels-Unique-Location-Fenced-In-Private-Beach.h92502496.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/3c0032f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/90570d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/88945e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/w1897h1258x3y5-0272e0a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Greenport Beach House right on the Sound! Breathtaking views Greenport 9.8/10 Exceptional (8) "We came for a girls trip and this property was perfect, had beautiful views and was close to everything...we very much enjoyed our stay!" CA $1,081 CA $1,736 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Greenport-Hotels-Gorgeous-Greenport-Beach-House-Right-On-The-Sound-Breathtaking-Views.h95352098.Hotel-Information) ![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1133h742x19y0-50746f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1109h758x16y4-b628a6e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1134h757x18y5-04d00f03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1169h768x0y0-20f93b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious multiples bedroom house in enchanting Calverton with WiFi, AC Calverton 8.4/10 Very good (7) "prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. " CA $696 CA $1,258 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Calverton-Hotels-Spacious-5-Bedroom-House-In-Enchanting-Calverton-With-WiFi.h108010988.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/119000000/118400000/118394700/118394686/cacdc9ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118400000/118394700/118394686/36da141c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/119000000/118400000/118394700/118394686/2478a032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118400000/118394700/118394686/922d4ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom apartment with WiFi, AC in enchanting Wading River Wading River CA $296 CA $661 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Wading-River-Hotels-Charming-2-Bedroom-Apartment-With-WiFi.h118394686.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/w1163h764x0y0-2c7bc0ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/cfaa160d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, foosball](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/f488ddfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/8c3e97ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches Water Mill 10/10 Exceptional (44) "Catherine was a great homeowner and made sure everything was organized prior to our arrival. She was very kind and easy to communicate with. She also was able to make sure we could have an early check in. " CA $2,804 CA $4,888 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Water-Mill-Hotels-6-Bedroom-Bridgehampton-Estate.h34005296.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/10ef3e76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/5f36ce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/a12114d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/52e5aba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautifully farmhouse Southold 10/10 Exceptional (3) "good experience" CA $837 CA $1,618 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Southold-Hotels-Magic-Place.h113098265.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e69dbcaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Petite King Room 7 Greenport 9.0/10 Wonderful (4) "Great job " CA $278 CA $424 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/4aaa8de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/20bbb653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/419a745d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/83198fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic New England home ,Reunions Beach pass Guilford 9.2/10 Wonderful (89) "House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining." CA $272 CA $615 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Guilford-Hotels-Historic-New-England-Home.h18760693.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/f8cef332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/a2326e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h954x0y0-9b5015ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h960x0y0-cce9554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard Saybrook Manor 9.6/10 Exceptional (133) "Great older house with everything you need to have a great time. Family event with 6 adults and 2 dogs enjoyed the house, the yard, and the area. Strongly recommend." CA $335 CA $701 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w906h683x58y0-bc7fef2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-6196bd68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-297b69ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-467ebb28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 5 Bedroom With Wi-fi And Air Condition Wainscott CA $1,853 CA $2,356 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Wainscott-Hotels-Cozy-5-Bedroom-With-Wi-Fi-And-Air-Condition.h119891409.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119970000/119966900/119966853/w509h683x258y0-4df3a872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119970000/119966900/119966853/15dd4e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119970000/119966900/119966853/60e9a277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/120000000/119970000/119966900/119966853/7ae5118d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East End Escape Flanders CA $587 CA $767 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Riverhead-Hotels-East-End-Escape.h119966853.Hotel-Information) ![Smart TV, fireplace, computer monitors, printers](https://images.trvl-media.com/lodging/116000000/115140000/115137600/115137583/a7ab8c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115140000/115137600/115137583/66b0cea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, computer monitors, printers](https://images.trvl-media.com/lodging/116000000/115140000/115137600/115137583/234b7a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115140000/115137600/115137583/423d6e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 Bedrooms! 4 Min to the Beach! HEATED POOL! Westhampton Beach 10/10 Exceptional (2) "awesome house and awesome host" CA $2,783 CA $4,077 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Westhampton-Beach-Hotels-5-Bedrooms-4-Min-To-The-Beach-HEATED-POOL.h115137583.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/w1035h701x17y0-8bcaee6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/680aee8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/7251e4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/30220c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Northfork Townhouse- walk to all Greenport 10/10 Exceptional (5) "Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again" CA $495 CA $963 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Greenport-Hotels-Greenport-Village-Townhouse-Walk-To-Town.h74202120.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/55e69dfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, internet](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/861024c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/bce95391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/d0d2900f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary Southampton Village Home Walking Distance to Town, Pool,... Southampton 10/10 Exceptional (15) "Just finished a 5 day stay. Best house rental ever! Great and thoughtful hosts. Super relaxing and extremely luxurious! Highly recommend!" CA $2,019 CA $2,931 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Southampton-Hotels-Contemporary-Southampton-Village-Home-Walking-Distance-To-Town.h50607334.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/bb644073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/4bd3774d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/ee30d2e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/6a96971c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Northfork Townhouse- walk to all/ newly renovated Greenport 9.6/10 Exceptional (9) "The place was as advertised and in great walking distance to everything in town! " CA $509 CA $980 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.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=2025-10-20&endDate=2025-10-21®ionId=183659&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%2FCutchogue-Private-Vacation-Homes.d183659-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCutchogue-Private-Vacation-Homes.d183659-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Cutchogue Hotel Reviews ![Water's Edge Resort & Spa](//images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Beautiful grounds, well maintained property. Our room was clean and comfortable. Definitely want to come back and extend our stay with family and friends. It’s a beautiful escape on the East Coast " [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Spark by Hilton Guilford](//images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg) ### Spark by Hilton Guilford 10/10 Excellent "Wow this has been an eye opener, what a fabulous hotel . It sparked my joy " [](https://expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![Bayview Resort](//images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2_y.jpg) ### Bayview Resort 10/10 Excellent "Drinks on the pier were lovely!" [](https://expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.Hotel-Information) ![The Sagaponack](//images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg) ### The Sagaponack 10/10 Excellent "I arrived late night for check-in. The staff text arranged for checking me in ahead of time and left a nice breakfast for me for the morning. Thank you!" [](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![Baron's Cove](//images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/560aa55e_y.jpg) ### Baron's Cove 10/10 Excellent "Parking was free and really easy. Great proximity to the main street of town—you can easily walk, but it's not too close where it gets loud at night. The front staff and cleaning team were all lovely and super helpful. We loved the coffee bar in the mornings. " [](https://expedia.ca/Sag-Harbor-Hotels-Barons-Cove.h1148848.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "Only issue....the refrigerator makes an annoying sound which is amlpified wearing hearing aids" [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Greenview Inn Riverhead](//images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/d1b868c8_y.jpg) ### Greenview Inn Riverhead 10/10 Excellent "All new decor . Very clean . Helpful staff" [](https://expedia.ca/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.Hotel-Information) ![The Shoals Suites and Slips](//images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg) ### The Shoals Suites and Slips 10/10 Excellent "Great quick stay" [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 10/10 Excellent "Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay." [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ## Find out more about Cutchogue ## Cutchogue Vacation Homes information | Number of reviews | 246 | | --- | --- | | Accommodation | 1849 Vacation Homes | | Lowest Price | CA $364 | | Highest Price | CA $8,949 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in North Fork](https://www.expedia.ca/5Star-North-Fork-Hotels.s50-0-d553248635074841663.Travel-Guide-Filter-Hotels) - [Hotels near Crescent Beach](https://www.expedia.ca/Crescent-Beach-Hotels.0-l553248621554204758-0.Travel-Guide-Filter-Hotels) - [Town of Southold Town Hotels](https://www.expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations) - [B&B in Fishers Island](https://www.expedia.ca/Fishers-Island-Bed-And-Breakfast.d1208-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Fishers Island](https://www.expedia.ca/Fishers-Island-Guest-Houses.d1208-aaGuestHouses.Travel-Guide-Accommodation) - 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