Vacation rentals in Town of Pound Ridge

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Top-rated vacation rentals in Town of Pound Ridge

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Top guest favorite

A serene view from the covered porch showcases a lush green lawn leading to the tranquil waters of Henderson Pond. Tall trees frame the scene, with dappled sunlight filtering through the leaves, creating a calm and inviting atmosphere.

Guest suite in Wilton

4.91 out of 5 average rating, 151 reviews

Serene Pond Views Charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Guest favorite

A round dining table with two transparent chairs is positioned near large windows that offer views of vibrant autumn foliage. A small vase with flowers decorates the table. Light enters through the open door, enhancing the bright and airy ambiance.

Guesthouse in Mahopac

4.95 out of 5 average rating, 249 reviews

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

Guest favorite

A charming cottage exterior is surrounded by lush greenery and autumn foliage. The two-story structure features a balcony adorned with potted plants. Large windows create a welcoming appearance, while the grassy area in front offers a peaceful outdoor setting.

Guesthouse in Wilton

4.97 out of 5 average rating, 130 reviews

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed and the living room has a futon couch which folds down. It’s perfect for 1-2 adults, can comfortably fit 3 people if one is a child.

Top guest favorite

A serene lake is framed by a densely forested hillside, reflecting vibrant autumn colors in the calm water. The sky reveals soft clouds and a bright blue backdrop. A canoe is positioned at the edge of the dock, inviting exploration of the tranquil surroundings.

Cottage in South Salem

5 out of 5 average rating, 116 reviews

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

Guest favorite

A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.

Cottage in Weston

4.97 out of 5 average rating, 160 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Top guest favorite

The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.

Guesthouse in Waccabuc

4.99 out of 5 average rating, 107 reviews

French Guest House in Waccabuc

A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

Superhost

A sunlit bedroom features a spacious bed topped with a neutral blanket and decorative pillows. Large windows allow natural light to filter in, casting soft shadows across the room. A wooden dresser with plants and framed artwork adds warmth to the inviting space.

Guest suite in Wilton

4.79 out of 5 average rating, 210 reviews

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Guest favorite

A quaint cottage is nestled among vibrant trees, showcasing rich foliage in shades of green and burgundy. A well-kept lawn surrounds the cottage, with a white door framed by flower beds. The serene setting invites relaxation in a natural environment.

Cottage in South Salem

4.96 out of 5 average rating, 248 reviews

Private cottage in horse country &1 hour from NYC!

Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)

Top guest favorite

A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.

Home in Pound Ridge

5 out of 5 average rating, 168 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

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, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Top guest favorite

The cottage is nestled among lush greenery, with a sloping yard leading to a rock bed. Large trees partially shade the structure, which features a combination of dark shingles and white trim. Windows allow soft light to illuminate the interior, enhancing the tranquil surroundings.

Cottage in Danbury

4.97 out of 5 average rating, 155 reviews

Fern Grove Cottage

If you’re looking for tranquility, this is the place for you! This charming cottage is located on a secluded country road. The cottage sits at the back of a gorgeous park-like property, and is near parks with hiking trails. This antique cottage has many modern renovations, providing convenience and comfort while maintaining the historic charm. This is the perfect getaway!

Guest favorite

A magnolia tree is in full bloom, featuring large, open pink and white flowers against a backdrop of greenery. The tree adds a vibrant touch to the garden area, with a stone pathway visible beside it, leading to more landscaped views.

Cottage in Stamford

4.97 out of 5 average rating, 203 reviews

Magnolia Cottage

Cozy cottage on a three acre wooded property in North Stamford. Main house shares the large circular driveway. A vast wall of windows facing a private garden invites one to relax in the knotty pine interior. Fully equipped. Perfect for a couple. We are available and friendly but tend to let guests have their private retreat unless they want information or help from us.

Top guest favorite

A rustic cottage is nestled amidst lush greenery, featuring a weathered wooden exterior and a large window that reflects the surrounding forest. Vibrant foliage and flowers adorn the landscaped yard, creating a peaceful natural setting.

Barn in Mount Kisco

4.91 out of 5 average rating, 586 reviews

NY Rustic Cottage Getaway

Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb