Places to stay in Pound Ridge

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Top-rated places to stay in Pound Ridge

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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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

4.9 out of 5 average rating, 146 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 gray sectional sofa is positioned next to two contrasting wooden coffee tables. A bowl of popcorn and decorative snacks are displayed on one table, while two glasses with iced drinks sit on the other. Decorative cushions with welcoming phrases add a cozy touch.

Apartment in Stamford

4.95 out of 5 average rating, 110 reviews

The Hillside Crib | 1 Bedroom Apt | Near Downtown

Enjoy this stylish 1-Bedroom apartment located near downtown Stamford. Walk to downtown to enjoy all it has to offer, from restaurants, shopping, UCONN of Stamford and more! Centrally located and a short train ride to New York City, our apartment offers everything you need for a comfortable stay in the area. We offer free parking on the premises and the train station is a 25 minute walk. Washer and Dryer included in the unit. This unique place has a style all its own! 3rd Fl. Unit use stairs.

Top guest favorite

An outdoor seating area is set among trees, featuring stone pathways and a gravel surface. A circular fire pit is surrounded by seating, and a small dining set with two chairs is positioned nearby. A grassy space adds greenery to the tranquil setting.

Guesthouse in Mahopac

4.95 out of 5 average rating, 238 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!

Top 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, 124 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.

Guest favorite

A clean bathroom is shown through an open door. It features a toilet, a shower area with white curtains, and a small cabinet mounted on the wall. Light beige tiles cover the floor, contributing to a bright and airy feel.

Apartment in Mount Kisco

4.93 out of 5 average rating, 187 reviews

Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train

This cozy apartment is on the lower level of a house, a 5 minute walk to town and the Harlem Line, Metro North Train stop. A separate entrance to the apt offers complete privacy. This gorgeous space has a fully equipped kitchen, bathroom, comfy twin beds . Located in the adorable town of Mt. Kisco, allowing you to take strolls to access restaurants, boutique shops, library, park and bars. It has the feel of a country retreat, a quaint town, and it's an easy commute to White Plains or NYC.

Guest favorite

A deck with four blue chairs overlooks the calm lake, flanked by tall trees and vibrant fall foliage. The natural stone wall in the foreground adds texture to the tranquil scene, enhancing the serene setting by the water.

Cottage in South Salem

4.96 out of 5 average rating, 135 reviews

Serene lake front cottage 1 hour from NYC

Serene minimalist cottage directly on Lake Oscaleta with spectacular waterfront and Mountain Lakes Park behind. Quiet, isolated and lost in the trees, you feel you are in Vermont or the Adirondacks. Yet it's only 1 hour from Manhattan, 10 minutes from restaurants. Kayak, canoe, fish, paddleboard. Cottage is elegant, cozy and winterized warm and the lake is effectively empty in the fall/winter/spring. Please note: because of an asthmatic child, we cannot accept any animals.

Guest favorite

Guesthouse in Pound Ridge

4.93 out of 5 average rating, 75 reviews

A Lovely Cottage in the Woods with Private Pool

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Top guest favorite

A treehouse structure is observed elevated among lush greenery, supported by a prominent tree. The exterior features dark siding, a distinct gable roof, and vibrant orange doors. A spiral staircase leads to the entrance, while a natural clearing surrounds the base.

Treehouse in Wallkill

4.99 out of 5 average rating, 320 reviews

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Guest favorite

Cottage in South Salem

4.95 out of 5 average rating, 238 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 well-maintained grass. Lounge chairs are positioned along the pool's edge under the shade of a large tree, creating a peaceful area for relaxation. The property is bordered by a wooden fence and offers expansive views of the surrounding landscape.

Home in Pound Ridge

5 out of 5 average rating, 165 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

A stacked washer and dryer unit is positioned against a light-colored wall, accompanied by a vintage poster framed and hung nearby. A small roll of paper towels rests on top of the dryer, while the surrounding area features wooden paneling for a rustic touch.

Cottage in Stamford

4.97 out of 5 average rating, 199 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 light-filled living area is visible, featuring a cozy seating arrangement with various cushions. A dining table with modern chairs is positioned nearby, illuminated by natural light streaming through multiple windows. The warm wood flooring adds to the inviting atmosphere.

Apartment in Bedford

4.97 out of 5 average rating, 32 reviews

Charming Cottage in historic Bedford Village

“This place emanates why I would live here!” - Robert 7/24 Just a 5 min walk to historic Bedford Village this detached one-bedroom cottage is surrounded by 200yr old Maple trees on the property of a 1840's farmhouse. Experience the hamlets of Westchester only 39 miles north of Manhattan and less than 10 min to the Bedford Hills - Harlem North train station.