Vacation Rentals By Owner In Pound Ridge, NY

Exceptional(5)

$815.42
/ Nightly

Private Vacation Home

beautiful contemporary house , only one hour from Manhattan

Pound Ridge, New York, United States
Seclusion and serenity in the quaint small town of Pound Ridge only an hour's drive from NYC.brBeautiful and renovated contemporary home sitting on 6.2 gorgeous acres of lush pine forest, across from reservoir with beautiful sunset views. This home offers unbeatable views, complete serenity, and total privacy and seclusion in one if the most desirable locations of Pound Ridge, a quaint village in Northern Westchester situated an hour away from New York City. Dining and shopping in the Village of Pound Ridge or Bedford is only a couple of miles away.

4
Bed

2
Bath

8
Sleeps

Exceptional(8)

$396.13
/ Nightly

Country House

1840 Farmhouse on 3 private acres with home theater! Pet Friendly!

Pound Ridge, New York, United States
Pet Friendly, Charming and spacious, recently renovated 1840 Farmhouse with 65inch LG OLED 4K TV with surround sound home theater! 3 private acres with walking (or mountain bike) trails on the property. Easy commute to NYC via Stamford CT Station 9 miles away with ample parking. Guests always comment on the floors and how stunning they are. FIREPIT for Smores all year round! A super peaceful retreat, or hook up your playlist to the Bluetooth surround sound and blast music with no neighbors to bother you. Very pet friendly with a partially fenced (road access is blocked by fencing) yard and a large, secure back porch to keep dogs if wet or muddy to dry out. Concerts in Bedford and Stamford all season long with fine dining at many famous restaurants in the local area (The Inn at Pound Ridge, by Jean Georges, The Bedford Post, br etc) Pound Ridge Preserve is excellent for hiking and camping, and horse riding. New Pete Dye designed golf course in Pound Ridge that is top 5 in the USA. Rowing Machine and Bicycle (54cm) Smart trainer with ZWIFT, ROUVY, etc for guest use.

2
Bed

2
Bath

6
Sleeps

Exceptional(49)

$1236.26
/ Nightly

Private Vacation Home

Over Sized Colonial on Private Road.

Pound Ridge, New York, United States
8900sqft. 5 bedrooms, 7 baths, 4 fireplaces, large screened in porch, large hot tub, huge stone patio, stone walls, lots of parking. Basketball net outdoors. Sleeps many!brEstate like. 1 Gigabit internet. Mesh Wifi full house. brbrThe basement if fully built out with 9' ceilings whole wall projector with Amazon Fire & Optimum TV + DVR. Foosball, ping-pong table, gym, bathroom with shower. brbrThere is a battery operated jeep in the garage with a spare battery for the little ones. brThere is a bike for kids around 7 years old & a teenager sized bike. Please bring helmets if you will use them. brbrNear great restaurants, wine stores, wineries, ocean, town pools, town parks, playgrounds, baseball, soccer etc sports fields, horse riding, fishing, architectural gems, playhouses, performance spaces, movie theaters. Surrounded by New Canaan, Ridgefield, South Salem. br

6
Bed

6
Bath

15
Sleeps

Exceptional(3)

$937.34
/ Nightly

Private Vacation Home

Pound Ridge Retreat: Private Trails, Fire Pit, Yoga + Fast Wi-Fi

Pound Ridge, New York, United States
Pound Ridge Retreat is a charming country home with private access to a large preserve and well-maintained hiking trails—plus a fire pit, yoga studio, and fast Wi-Fi for an easy weekend reset or work-from-anywhere getaway.brbrIdeal for hikers, families, and small groups who want privacy, comfort, and space to unwind.brbrHighlightsbr• Private trail access to a large preserve (hike right from the property)br• Yoga studio with mats includedbr• Game room with ping-pong + board gamesbr• Large deck with picnic table overlooking a spacious yardbr• Fire pit + Adirondack chairs for cool eveningsbr• Charcoal grill for outdoor dinnersbrbrKitchen & diningbrWell-equipped kitchen for real meals and group cooking, including a Cuisinart, blender, waffle iron, hand mixer, toaster oven, coffee maker, grinder, and kettle—plus full cookware, dishes, and serving pieces.brbrWork-from-home readybrHigh-speed Wi-Fi throughout the house (250+ Mbps). Every bedroom has a dedicated desk or table for working.brbrSleeping & bathsbr4 bedrooms (sleeps 7) • 4 full bathroomsbrKing ensuite with double sinks + large shower; Queen bath with tub + shower; two additional full baths with showers.brbrLocationbrAbout 1 hour from NYC • ~20 minutes to Stamford • ~5 minutes to the hamlet of Pound Ridge

4
Bed

4
Bath

7
Sleeps

Exceptional(5)

$815.42
/ Nightly

Private Vacation Home

beautiful contemporary house , only one hour from Manhattan

Pound Ridge, New York, United States
Seclusion and serenity in the quaint small town of Pound Ridge only an hour's drive from NYC.brBeautiful and renovated contemporary home sitting on 6.2 gorgeous acres of lush pine forest, across from reservoir with beautiful sunset views. This home offers unbeatable views, complete serenity, and total privacy and seclusion in one if the most desirable locations of Pound Ridge, a quaint village in Northern Westchester situated an hour away from New York City. Dining and shopping in the Village of Pound Ridge or Bedford is only a couple of miles away.

4
Bed

2
Bath

8
Sleeps

Exceptional(8)

$396.13
/ Nightly

Country House

1840 Farmhouse on 3 private acres with home theater! Pet Friendly!

Pound Ridge, New York, United States
Pet Friendly, Charming and spacious, recently renovated 1840 Farmhouse with 65inch LG OLED 4K TV with surround sound home theater! 3 private acres with walking (or mountain bike) trails on the property. Easy commute to NYC via Stamford CT Station 9 miles away with ample parking. Guests always comment on the floors and how stunning they are. FIREPIT for Smores all year round! A super peaceful retreat, or hook up your playlist to the Bluetooth surround sound and blast music with no neighbors to bother you. Very pet friendly with a partially fenced (road access is blocked by fencing) yard and a large, secure back porch to keep dogs if wet or muddy to dry out. Concerts in Bedford and Stamford all season long with fine dining at many famous restaurants in the local area (The Inn at Pound Ridge, by Jean Georges, The Bedford Post, br etc) Pound Ridge Preserve is excellent for hiking and camping, and horse riding. New Pete Dye designed golf course in Pound Ridge that is top 5 in the USA. Rowing Machine and Bicycle (54cm) Smart trainer with ZWIFT, ROUVY, etc for guest use.

2
Bed

2
Bath

6
Sleeps

Exceptional(49)

$1236.26
/ Nightly

Private Vacation Home

Over Sized Colonial on Private Road.

Pound Ridge, New York, United States
8900sqft. 5 bedrooms, 7 baths, 4 fireplaces, large screened in porch, large hot tub, huge stone patio, stone walls, lots of parking. Basketball net outdoors. Sleeps many!brEstate like. 1 Gigabit internet. Mesh Wifi full house. brbrThe basement if fully built out with 9' ceilings whole wall projector with Amazon Fire & Optimum TV + DVR. Foosball, ping-pong table, gym, bathroom with shower. brbrThere is a battery operated jeep in the garage with a spare battery for the little ones. brThere is a bike for kids around 7 years old & a teenager sized bike. Please bring helmets if you will use them. brbrNear great restaurants, wine stores, wineries, ocean, town pools, town parks, playgrounds, baseball, soccer etc sports fields, horse riding, fishing, architectural gems, playhouses, performance spaces, movie theaters. Surrounded by New Canaan, Ridgefield, South Salem. br

6
Bed

6
Bath

15
Sleeps

Exceptional(3)

$937.34
/ Nightly

Private Vacation Home

Pound Ridge Retreat: Private Trails, Fire Pit, Yoga + Fast Wi-Fi

Pound Ridge, New York, United States
Pound Ridge Retreat is a charming country home with private access to a large preserve and well-maintained hiking trails—plus a fire pit, yoga studio, and fast Wi-Fi for an easy weekend reset or work-from-anywhere getaway.brbrIdeal for hikers, families, and small groups who want privacy, comfort, and space to unwind.brbrHighlightsbr• Private trail access to a large preserve (hike right from the property)br• Yoga studio with mats includedbr• Game room with ping-pong + board gamesbr• Large deck with picnic table overlooking a spacious yardbr• Fire pit + Adirondack chairs for cool eveningsbr• Charcoal grill for outdoor dinnersbrbrKitchen & diningbrWell-equipped kitchen for real meals and group cooking, including a Cuisinart, blender, waffle iron, hand mixer, toaster oven, coffee maker, grinder, and kettle—plus full cookware, dishes, and serving pieces.brbrWork-from-home readybrHigh-speed Wi-Fi throughout the house (250+ Mbps). Every bedroom has a dedicated desk or table for working.brbrSleeping & bathsbr4 bedrooms (sleeps 7) • 4 full bathroomsbrKing ensuite with double sinks + large shower; Queen bath with tub + shower; two additional full baths with showers.brbrLocationbrAbout 1 hour from NYC • ~20 minutes to Stamford • ~5 minutes to the hamlet of Pound Ridge

4
Bed

4
Bath

7
Sleeps

Exceptional(9)

$944.83
/ Nightly

Guest House

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Pound Ridge, New York, United States
Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, evening stargazing by the outdoor fire pit or unwind in the pool side sauna. Perfect for families, small groups, or couples seeking a peaceful nature retreat.brbrLocated in Westchester County, our renovated guesthouse is part of a historic 200-year-old dairy farm, cherished by the same family for over 11 generations.brbrInspired by travel and the concept of slow living, our guesthouse provides a tranquil escape—a place to pause, enjoy simple moments, and immerse yourself in nature's wonders. Whether relaxing by the pool on hot summer days, enjoying the vibrant colors of autumn by the fire pit, or sledding on snowy hills in winter, each season offers its unique charm.brbrWe feel privileged to care for this natural beauty and are grateful to share it with our guests. We hope you find it as special as we do.brbrFor more images & videos visit insta @sweetbriarguesthousebrbrThe ground floor features two separate living rooms, a dining area, a kitchen, a side hallway leading to a full bathroom, and a bedroom.brbrLarge picture windows in the main living and dining area offer serene views of the meadow and trees, with L-shaped seating around the wood-burning stove adorned with art and photography.brbrAdjacent to the kitchen, the second living room includes additional seating and a queen-sized pull-out sleeper sofa facing a large internet-connected TV, perfect for relaxation or separate TV viewing.brbrThe well-equipped kitchen boasts new appliances such as an induction stove and Vitamix, alongside kid-friendly utensils and various coffee makers. Meals can be enjoyed at the breakfast nook or the spacious oak dining table, ideal for gatherings.brbrOutside, a private dining area and fire pit provide a secluded setting for evening meals, complemented by a propane grill and string lights.brbrUpstairs, the south-facing bedroom features a king-size bed, a seating area, and a Juliet balcony overlooking the pool. Guests might even spot our resident groundhog in the early mornings. The second bedroom includes two twin XL beds and a skylight for stargazing and ample natural light.brbrAccommodating up to 7 guests with three bedrooms and a sleeper sofa, the guesthouse offers two full-size bathrooms stocked with Aēsop products and bidet toilets, including a full-size shower on the ground floor and a bath/shower in the upper floor bathroom.brbrAdditional amenities include an upper-floor utility room with a full-size washer and dryer, high-speed internet (great for remote work), a 20'x40' heated saltwater pool, a 4 person electric cedar sauna, an EV charger, and three dedicated guest parking spots.brbrConvenient delivery options are available from Whole Foods, Fresh Direct, Grubhub, and Uber Eats.brLocated just 10 minutes from Bedford NY, Ridgefield CT, Scotts Corners NY, Waccabuc NY, and South Salem NY, and 20 minutes from New Canaan CT, Katonah NY, Mount Kisco NY, and Bedford Hills NY.brbrbrWhile we live on the property, the guesthouse is designed to ensure maximum guest privacy. We respect your space but are available for any questions or concerns.brbrFeel free to explore the surroundings, but please respect the areas around our private residence (white house) and work studio (grey barn).brbrThe guesthouse grounds, spanning over 1 acre, are exclusively reserved for our guests.brbrGuests share the pool with the owners.brbrPlease take a moment to read the entire listing before booking. If you have any questions, please ask us or check out our FAQ section below beforehand. A short-term rental agreement must be signed in addition to the VRBO booking. Kindly adhere to all house rules outlined in the agreement and the House Book provided after booking. Thank you!brbrFAQbrWHEN IS THE POOL OPEN brGuests have access to the pool starting Memorial weekend through sometime in September. Please note: Contact us for the closing date before booking. The outdoor shower is available during the pool season.brIS THE POOL SHARED brWhile guests share the pool with the hosts, we ensure that guest time in the pool is always respected.brARE GUESTS ALLOWED brOnly registered guests are permitted on the property.brARE PARTIES/EVENTS ALLOWED brNo.brARE PETS ALLOWED brDogs are allowed but must be included in the initial booking. Dogs should be house-trained and well-behaved. We charge a $50/pet cleaning fee per stay (this covers up to 2 pets).

3
Bed

2
Bath

7
Sleeps

Exceptional(6)

$1456.82
/ Nightly

Private Vacation Home

✔️ Couples escapes ✔️ Family gatherings ✔️ Private retreats ✔️ Celebration stays

Pound Ridge, New York, United States
MOUNTAIN VISTA LUXURY RETREATbrbrAn elevated retreat designed for unforgettable group staysbrbrA private luxury retreat with panoramic views, natural light, and seamless indoor-outdoor living.brbrEnjoy two gourmet kitchens, open living spaces, and curated interiors. Amenities include a private outdoor spa with hot tub, full gym, and AMC-style theater with VIP seating.brbrThe game room features a pool table, poker table, and arcade games. Outdoors, relax on multiple decks, a stone patio for gatherings, and a peaceful mountain setting.brbrThe perfect place for you!

5
Bed

4
Bath

10
Sleeps

$1079.28
/ Nightly

Private Vacation Home

Peaceful Pound Ridge Summer Retreat w/ Pool & 5 Bedrooms, 65 min to NYC

Pound Ridge, New York, United States
Escape to your own private sanctuary in Pound Ridge, NY. Set on 2 acres of wooded property, shielded from neighbors and surrounded by nature, this light-filled retreat offers the perfect blend of luxury and family comfort.brWith floor-to-ceiling windows, French doors opening to a wrap-around deck, balconies, and a heated competition-size pool, this home is designed for unforgettable summer living.brAvailable July & August brOffers a separate apartment, ideal for a live-in nanny or friends.brbrThis 5-bedroom house can sleep up to 10 people. With fully renovated bathrooms featuring bathtubs and showers, guests enjoy plenty of space and comfort. Downstairs exits to the pool with zero steps, as a separate studio with a king bed, large sofas, a mini kitchenette, and a shower. Outside features a large wraparound balcony for gatherings and quiet dinners. Olympic-sized heated pool for endless summer fun. Kick back, relax, and enjoy everything Pound Ridge and our amazing house have to offer.

5
Bed

3
Bath

10
Sleeps

Exceptional(6)

$1456.82
/ Nightly

Private Vacation Home

✔️ Couples escapes ✔️ Family gatherings ✔️ Private retreats ✔️ Celebration stays

Pound Ridge, New York, United States
MOUNTAIN VISTA LUXURY RETREATbrbrAn elevated retreat designed for unforgettable group staysbrbrA private luxury retreat with panoramic views, natural light, and seamless indoor-outdoor living.brbrEnjoy two gourmet kitchens, open living spaces, and curated interiors. Amenities include a private outdoor spa with hot tub, full gym, and AMC-style theater with VIP seating.brbrThe game room features a pool table, poker table, and arcade games. Outdoors, relax on multiple decks, a stone patio for gatherings, and a peaceful mountain setting.brbrThe perfect place for you!

5
Bed

4
Bath

10
Sleeps

$1079.28
/ Nightly

Private Vacation Home

Peaceful Pound Ridge Summer Retreat w/ Pool & 5 Bedrooms, 65 min to NYC

Pound Ridge, New York, United States
Escape to your own private sanctuary in Pound Ridge, NY. Set on 2 acres of wooded property, shielded from neighbors and surrounded by nature, this light-filled retreat offers the perfect blend of luxury and family comfort.brWith floor-to-ceiling windows, French doors opening to a wrap-around deck, balconies, and a heated competition-size pool, this home is designed for unforgettable summer living.brAvailable July & August brOffers a separate apartment, ideal for a live-in nanny or friends.brbrThis 5-bedroom house can sleep up to 10 people. With fully renovated bathrooms featuring bathtubs and showers, guests enjoy plenty of space and comfort. Downstairs exits to the pool with zero steps, as a separate studio with a king bed, large sofas, a mini kitchenette, and a shower. Outside features a large wraparound balcony for gatherings and quiet dinners. Olympic-sized heated pool for endless summer fun. Kick back, relax, and enjoy everything Pound Ridge and our amazing house have to offer.

5
Bed

3
Bath

10
Sleeps

$937.34
/ Nightly

Private vacation home

Pound Ridge Retreat: Private Trails, Fire Pit, Yoga + Fast Wi-Fi

Pound Ridge, New York, United States

4
Bed

4
Bath

7
Sleeps

$944.83
/ Nightly

Guest house

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Pound Ridge, New York, United States

3
Bed

2
Bath

7
Sleeps

$1456.82
/ Nightly

Private vacation home

✔️ Couples escapes ✔️ Family gatherings ✔️ Private retreats ✔️ Celebration stays

Pound Ridge, New York, United States

5
Bed

4
Bath

10
Sleeps

$396.13
/ Nightly

Country House

1840 Farmhouse on 3 private acres with home theater! Pet Friendly!

Pound Ridge, New York, United States

2
Bed

2
Bath

6
Sleeps

$815.42
/ Nightly

Private vacation home

beautiful contemporary house , only one hour from Manhattan

Pound Ridge, New York, United States

4
Bed

2
Bath

8
Sleeps

$1236.26
/ Nightly

Private vacation home

Over Sized Colonial on Private Road.

Pound Ridge, New York, United States

6
Bed

6
Bath

15
Sleeps

$1079.28
/ Nightly

Private vacation home

Peaceful Pound Ridge Summer Retreat w/ Pool & 5 Bedrooms, 65 min to NYC

Pound Ridge, New York, United States

5
Bed

3
Bath

10
Sleeps