Title: Pound Ridge, NY Vacation Homes from $197 | Expedia.com [Pound Ridge Travel Guide](https://expedia.com/Pound-Ridge.dx3000449463)[Hotels in Pound Ridge](https://expedia.com/Pound-Ridge-Hotels.d3000449463.Travel-Guide-Hotels)[Vacation Rentals in Pound Ridge](https://expedia.com/Pound-Ridge-Vacation-Rentals.d3000449463.Travel-Guide-VacationRentals)[Flights to Pound Ridge](https://expedia.com/Cheap-Flights-To-Pound-Ridge.d3000449463.Travel-Guide-Flights)[Car Rentals in Pound Ridge](https://expedia.com/Car-Rentals-In-Pound-Ridge.d3000449463.Car-Rental-Guide)[Pound Ridge Vacation Packages](https://expedia.com/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) ![](https://images.trvl-media.com/place/3000449463/a0fa9f4e-2071-432b-bc85-3dd175484ad9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=3000449463&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=3000449463&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=3000449463&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=3000449463&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) ## Our top choices for Pound Ridge vacation homes ![Property grounds](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/7ce63cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/e1560e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/5b614a2b.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) ### 2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich. [](https://www.expedia.com/Greenwich-Hotels-2-Bedroom-And-1-Full-Bath-In-Lakeside-Home-With-Private-Dock.h114606188.Hotel-Information) Greenwich 9.8/10 Exceptional (27 reviews) "We enjoyed our stay here. The rooms are clean and comfortable. The hosts are very friendly and hospitable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph M. $211 nightly $239 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Greenwich-Hotels-2-Bedroom-And-1-Full-Bath-In-Lakeside-Home-With-Private-Dock.h114606188.Hotel-Information) ![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.com/Charming.h111683284.Hotel-Information) Shelton 9.0/10 Wonderful (2 reviews) "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. $174 nightly $197 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Charming.h111683284.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) ![Exterior](https://images.trvl-media.com/lodging/96000000/95900000/95891300/95891227/d50b7da5.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) ![Smart TV, books](https://images.trvl-media.com/lodging/96000000/95900000/95891300/95891227/48a60c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marine Theme - 4 BR - Backyard - Fire pit [](https://www.expedia.com/Bridgeport-Hotels-Marine-Theme-4-BR-Backyard-Fire-Pit.h95891227.Hotel-Information) North End 9.8/10 Exceptional (8 reviews) "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. $350 nightly $397 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Bridgeport-Hotels-Marine-Theme-4-BR-Backyard-Fire-Pit.h95891227.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) ![Dining](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/416c2b95.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) ### Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike. [](https://www.expedia.com/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information) Carmel Hamlet 9.8/10 Exceptional (13 reviews) "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. $338 nightly $366 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.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/110000000/109390000/109381700/109381685/4388309b.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) ![Exterior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/d8805194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Country outside the city " 3 bedrooms 2 full bathrooms [](https://www.expedia.com/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information) Holmes 9.6/10 Exceptional (4 reviews) "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. $517 nightly $585 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118330000/118324400/118324337/85be0cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118330000/118324400/118324337/7759d647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118330000/118324400/118324337/1afa8516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/119000000/118330000/118324400/118324337/945e4ee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated Retreat with Heated Pool [](https://www.expedia.com/Redding-Hotels-Renovated-Retreat-With-Heated-Pool.h118324337.Hotel-Information) Redding 10/10 Exceptional (2 reviews) "Beautiful house, very clean, spacious and a great host!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alejandro A. $466 nightly $528 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Redding-Hotels-Renovated-Retreat-With-Heated-Pool.h118324337.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/05c87dfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/67aed9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/4390f269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/67ba7f30.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.com/New-Fairfield-Hotels-Peaceful-All-Season-Lake-Community-Home.h100167349.Hotel-Information) New Fairfield 10/10 Exceptional (18 reviews) "Great location and condition. Roome enough for everyone." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher H. $443 nightly $502 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/New-Fairfield-Hotels-Peaceful-All-Season-Lake-Community-Home.h100167349.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) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/2730f6d1.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/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.com/Stamford-Hotels-Charming-2-Bedroom-House-In-Fabulous-Stamford-With-AC.h112364813.Hotel-Information) Waterside 10/10 Exceptional (11 reviews) "Fantastic place. We had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara C. $290 nightly $328 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Stamford-Hotels-Charming-2-Bedroom-House-In-Fabulous-Stamford-With-AC.h112364813.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 | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/7eecbab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium House, Garden View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](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) ### Beechmont - Perfect for Family Retreat! [](https://www.expedia.com/Bridgeport-Hotels-Beechmont.h119248411.Hotel-Information) North End $1,200 nightly $1,380 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Bridgeport-Hotels-Beechmont.h119248411.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/383d7f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/1ec1e18e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/31a3b952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/97000000/96140000/96133300/96133224/8da70dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage with Fire Pit, near Beach [](https://www.expedia.com/Fairfield-Hotels-Family-Friendly-Renovated.h96133224.Hotel-Information) Fairfield 10/10 Exceptional (27 reviews) "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. $433 nightly $490 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Fairfield-Hotels-Family-Friendly-Renovated.h96133224.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) ![Exterior](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/72602a0e.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) ![Interior](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/b5a9021c.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.com/Bridgeport-Hotels-Charming-Colonial-Retreat-Perfect-For-Family-Getaways.h112048293.Hotel-Information) North End 9.6/10 Exceptional (8 reviews) "Very clean house. set up very nicely, landlord was very responsive and helpful. perfect for what we needed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy H. $1,291 nightly $1,461 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Bridgeport-Hotels-Charming-Colonial-Retreat-Perfect-For-Family-Getaways.h112048293.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/d1c3f1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/a3eab038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/59dbec3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110280000/110276000/110275967/03f47a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated Cape Near beach, with Fire Pit and BBQ [](https://www.expedia.com/Fairfield-Hotels-Renovated-Retreat-WFire-Pit.h110275967.Hotel-Information) Fairfield 10/10 Exceptional (11 reviews) "Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary G. $424 nightly $480 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Fairfield-Hotels-Renovated-Retreat-WFire-Pit.h110275967.Hotel-Information) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/874d2ade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/f6f4b3c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/5185160d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/107000000/106570000/106560900/106560827/6b5ce507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Cottage with 4 King Beds and Fire Pit [](https://www.expedia.com/Norwalk-Hotels-Family-Friendly.h106560827.Hotel-Information) Historic District 10/10 Exceptional (10 reviews) "Stayed with our adult children for a family wedding. Everyone enjoyed the spotless, attractive & appointed home with lovely king beds in all the rooms. It was a treat!Host was very attentive, would highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy B. $450 nightly $510 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Norwalk-Hotels-Family-Friendly.h106560827.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) ![Dining](https://images.trvl-media.com/lodging/88000000/87230000/87226100/87226001/2106b7f5.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) ![Exterior detail](https://images.trvl-media.com/lodging/88000000/87230000/87226100/87226001/72e8d656.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.com/Bridgeport-Hotels-Golden-Colonial-Home-Family-Friendly.h87226001.Hotel-Information) Brooklawn - St. Vincent 7.0/10 Good (14 reviews) "This rental was great accommodation" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alma B. $263 nightly $297 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Bridgeport-Hotels-Golden-Colonial-Home-Family-Friendly.h87226001.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76820000/76813800/76813717/218349d2.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/77000000/76820000/76813800/76813717/4740d81d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76820000/76813800/76813717/9f1b2838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76820000/76813800/76813717/7905bebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious [](https://www.expedia.com/Fairfield-Hotels-Grand-Fairfield-Getaway-5BR-Fam-Friendly-Near-I95Shops-SpaciousGracious.h76813717.Hotel-Information) Tunxis Hill 9.4/10 Exceptional (20 reviews) "The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily K. $656 nightly $742 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Fairfield-Hotels-Grand-Fairfield-Getaway-5BR-Fam-Friendly-Near-I95Shops-SpaciousGracious.h76813717.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) ![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) ![Smart TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/102000000/101740000/101736200/101736107/be624494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The B&W Haven 5BR Home with yard theater + Office [](https://www.expedia.com/Bridgeport-Hotels-The-BW-Haven-5BR-Home-With-Yard-Theater-Office.h101736107.Hotel-Information) Brooklawn - St. Vincent 9.4/10 Exceptional (8 reviews) "Lovely home with plenty of room! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David S. $593 nightly $672 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Bridgeport-Hotels-The-BW-Haven-5BR-Home-With-Yard-Theater-Office.h101736107.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) ![Interior](https://images.trvl-media.com/lodging/115000000/114300000/114291600/114291600/9f9cf405.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) ![Exterior](https://images.trvl-media.com/lodging/115000000/114300000/114291600/114291600/d2a199e7.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.com/Fairfield-Hotels-Luxury-Estate-W-Heated-Pool.h114291600.Hotel-Information) Tunxis Hill 10/10 Exceptional (1 review) "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. $1,747 nightly $1,965 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/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) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/3745699f.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) ![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/449fc3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary Cozy Cottage [](https://www.expedia.com/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information) Lake Peekskill 10/10 Exceptional (31 reviews) "Very clean comfortable quiet place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mauro C. $367 nightly $420 total Feb 14 - Feb 15 Total with taxes and fees [](https://www.expedia.com/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/86ae4160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/185a287e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/a65c4dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/79000000/78410000/78400400/78400391/1e85a3aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near... [](https://www.expedia.com/Stamford-Hotels-Modern-3-Bdrm-Home-W-Parking.h78400391.Hotel-Information) West Side 9.4/10 Exceptional (6 reviews) "Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dave J. $443 nightly $475 total Feb 11 - Feb 12 Total with taxes and fees [](https://www.expedia.com/Stamford-Hotels-Modern-3-Bdrm-Home-W-Parking.h78400391.Hotel-Information) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/6e503ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/11e211e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/ae91b214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/w3000h1944x0y0-bf620bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW 45 Wolden Rd Ossining NY 10562 [](https://www.expedia.com/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information) Ossining $836 nightly $932 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.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.com/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24®ionId=3000449463&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Pound+Ridge%2C+New+York%2C+United+States+of+America®ionId=3000449463&latLong=41.208443%2C-73.574821&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APART_HOTEL) Apartments [](https://www.expedia.com/Hotel-Search?destination=Pound+Ridge%2C+New+York%2C+United+States+of+America®ionId=3000449463&latLong=41.208443%2C-73.574821&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APARTMENT) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Pound+Ridge%2C+New+York%2C+United+States+of+America®ionId=3000449463&latLong=41.208443%2C-73.574821&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VACATION_HOME) Villas [](https://www.expedia.com/Hotel-Search?destination=Pound+Ridge%2C+New+York%2C+United+States+of+America®ionId=3000449463&latLong=41.208443%2C-73.574821&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VILLA) Condos [](https://www.expedia.com/Hotel-Search?destination=Pound+Ridge%2C+New+York%2C+United+States+of+America®ionId=3000449463&latLong=41.208443%2C-73.574821&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CONDO) Cottages [](https://www.expedia.com/Hotel-Search?destination=Pound+Ridge%2C+New+York%2C+United+States+of+America®ionId=3000449463&latLong=41.208443%2C-73.574821&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=COTTAGE) Cabins [](https://www.expedia.com/Hotel-Search?destination=Pound+Ridge%2C+New+York%2C+United+States+of+America®ionId=3000449463&latLong=41.208443%2C-73.574821&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CABIN) Chalets [](https://www.expedia.com/Hotel-Search?destination=Pound+Ridge%2C+New+York%2C+United+States+of+America®ionId=3000449463&latLong=41.208443%2C-73.574821&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CHALET) ![](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.com/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.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPound-Ridge-Private-Vacation-Homes.d3000449463-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Pound Ridge Hotel Reviews ![HYATT house White Plains](https://images.trvl-media.com/lodging/1000000/430000/427300/427283/458cd7c2_y.jpg) ### HYATT house White Plains 10/10 Excellent "Nice room, good breakfast , nice staff" [](https://expedia.com/White-Plains-Hotels-HYATT-House-White-Plains.h427283.Hotel-Information) ![Hotel Zero Degrees Danbury](https://images.trvl-media.com/lodging/17000000/16270000/16263900/16263812/1fb60e7f_y.jpg) ### Hotel Zero Degrees Danbury 10/10 Excellent "Gorgeous and clean rooms. Great breakfast in the morning. Delicious restaurant in the hotel. One of my favorite stays hands down!" [](https://expedia.com/Danbury-Hotels-Hotel-Zero-Degrees-Danbury.h16263812.Hotel-Information) ![Hampton Inn White Plains/Tarrytown](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/d5b0e16e_y.jpg) ### Hampton Inn White Plains/Tarrytown 10/10 Excellent "Good stay. Love the cookies" [](https://expedia.com/White-Plains-Hotels-Hampton-Inn-White-Plains.h23291.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 "Room was nice and clean also babe very good heat . Staff was very nice and friendly will be visiting again " [](https://expedia.com/White-Plains-Hotels-Ardsley-Acres-Hotel-Westchester.h1166864.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 "everything was great " [](https://expedia.com/Nyack-Hotels-West-Gate-Inn-Nyack.h5843352.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 " [](https://expedia.com/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![Tarrytown House Estate](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg) ### Tarrytown House Estate 10/10 Excellent "Amazing courteous and professional staff very good p" [](https://expedia.com/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![Hampton Inn & Suites Yonkers - Westchester](https://images.trvl-media.com/lodging/16000000/15740000/15731000/15730982/2770772f_y.jpg) ### Hampton Inn & Suites Yonkers - Westchester 10/10 Excellent "We stayed at this Hampton Inn location many times on our trips up and down east coast. We even have our favorite room. The staff was extremely friendly, always welcoming you with a smile and eager to help you make your stay comfortable. Breakfast choices are good. Just wish that that Hilton corporation would move away from the use of disposable plates, cups and utensils to something more environmentally friendly. " [](https://expedia.com/White-Plains-Hotels-Hampton-Inn-Suites-Yonkers-Westchester.h15730982.Hotel-Information) ![Hotel Nyack, a JdV by Hyatt Hotel](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/a38df02c_y.jpg) ### Hotel Nyack, a JdV by Hyatt Hotel 10/10 Excellent "Very quiet and the staff stayed out of my way as I wanted. Beautiful property and the price was exceptional. Will make this my go to whenever I am in the Hudson Valley. " [](https://expedia.com/Nyack-Hotels-Hotel-Nyack.h11943081.Hotel-Information) ## Find out more about Pound Ridge ## Pound Ridge Vacation Homes information | Number of reviews | 208 | | ----------------- | ------------------ | | Accommodation | 361 Vacation Homes | | Lowest Price | $197 | | Highest Price | $1,965 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [New York Hotels ](https://www.expedia.com/New-York-Hotels.d178293.Travel-Guide-Hotels) - [B&B in Bedford ](https://www.expedia.com/Bedford-Bed-And-Breakfast.d553248628384502029-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Bedford ](https://www.expedia.com/Bedford-Cottages.d553248628384502029-aaCottages.Travel-Guide-Accommodation) - [Motels in Bedford ](https://www.expedia.com/Bedford-Motels.d553248628384502029-aaMotels.Travel-Guide-Accommodation) - [Condo Rentals in Bedford ](https://www.expedia.com/Bedford-Condos.d553248628384502029-aaCondos.Travel-Guide-Accommodation) - 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