Vacation rentals in Wooster Mountain

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Wooster Mountain

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Superhost

A serene beach view features soft sandy shores leading to calm waters. A small wooden bench is positioned in the foreground, while a sailboat glides gracefully on the horizon. Gentle waves can be seen lapping at the shoreline under a clear blue sky.

Home in Milford

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

Superhost

Home in Roxbury

5 out of 5 average rating, 10 reviews

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

Guest favorite

Chalet in Goshen

4.89 out of 5 average rating, 141 reviews

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

Superhost

Two comfortable chairs are positioned on a spacious porch, offering a clear view of the beach and ocean. The horizon is visible in the distance, with calm waters under a blue sky dotted with clouds.

Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

Top guest favorite

A spacious outdoor dining area features a large wooden table surrounded by matching chairs. Sunlight illuminates the area, showcasing a well-maintained yard with a manicured hedge and a small garden shed visible in the background.

Home in Northport

4.94 out of 5 average rating, 114 reviews

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

Guest favorite

A lakeside retreat is nestled among lush greenery, featuring a spacious deck with blue seating. A gentle slope leads to the water's edge, where a small area is provided for relaxing. A large tree casts shade over the grassy yard, enhancing the natural setting.

Home in Putnam Valley

4.97 out of 5 average rating, 58 reviews

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Top guest favorite

Home in Farmington

5 out of 5 average rating, 60 reviews

Lake Escape: Lake Cottage Charm, Lake Front, AC

Direct lakefront access with gorgeous views on a private lake. This beautiful 1930's lakefront cottage was fully renovated and reimagined by its owners in 2021. Custom architectural trim and details can be found throughout blending this homes' heritage with modern amenities. 2 bedrooms, eat-in kitchen and window seat nook, 2 full baths, custom barn doors and cabinetry, a reimagined sunroom, beautiful views on 100' of accessible lake frontage with outdoor patio, 1 mile from town center.

Superhost

A charming building is illuminated by soft evening light, surrounded by blossoming trees adorned with twinkling lights. Outdoor seating is visible, inviting guests to enjoy the vibrant atmosphere of the town. The sky transitions to a serene twilight blue, enhancing the scene.

Guest suite in Branford

4.9 out of 5 average rating, 99 reviews

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

Top guest favorite

Home in New Paltz

5 out of 5 average rating, 38 reviews

Luxury Home with Mountain Views

This sprawling home with a spectacular Mohonk view is minutes from the shops and restaurants in the Village of New Paltz. It is within walking distance of the River to Ridge Trail and Mohonk Preserve, offering hundreds of acres of outdoor recreation. This house is designed for entertaining and lounging, with plenty of room for everyone. Perfect for those seeking a vacation with family or friends, it allows for gathering and privacy. The house is impressive inside and out.

Superhost

Large glass doors provide a view of the surrounding woods and sunset, creating a bright and airy ambiance. A coffee table is positioned in front, accompanied by modern chairs and a dining table, enhancing the spacious and inviting feel of the living area.

Cabin in Rhinebeck

4.89 out of 5 average rating, 371 reviews

Sunset Bungalow-Mt views on 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, and comfortable bedroom- learn more at cascadafarm.com

Superhost

A serene bathroom features a two-person soaking tub situated beside large windows that allow ample natural light. A sleek black faucet stands above the tub, complemented by a wooden tray holding spa essentials. Fresh towels are neatly arranged on a foldable rack nearby.

Home in Rosendale

4.75 out of 5 average rating, 36 reviews

Luxury Retreat on Rondout Creek- Wedding Central!

Escape the city and experience small-town mountain living in this newly-renovated, 3-story 1880's classic home, Nestled between the Rondout Creek and picturesque Main Street in Rosendale. Just 1.5 hours from Manhattan, and in the heart of the Hudson Valley, this is perfect for a peaceful getaway, or wedding overflow for nearby Mohonk Mountain House, Hutton Brickyards and Inness resorts. Large enough for the whole family to enjoy the winter wonderland on the river!

Guest favorite

A spacious outdoor deck is furnished with a large sectional seating area, featuring soft cushions for comfort. A glass-top coffee table is positioned at the center. The view includes a glimpse of the nearby beach and coastal structures.

Home in Milford

4.91 out of 5 average rating, 57 reviews

Modern Beach Getaway

This 4 bedroom, 3 bathroom vacation rental in Milford, CT, boasts beautiful hardwood floors, high ceilings, and an open-concept living area perfect for entertaining guests. Each bedroom is tastefully decorated, and the fenced-in private yard features a deck and firepit area. The rental is located across the street from a private beach and is a short drive from local shops and restaurants, making it the ideal spot for a summer getaway.

0 of 0 items showing

What guests are saying

Spacious, Quiet 4 Bedroom + All Season Hot Tub

4.98 out of 5 average rating, 64 reviews4 days ago

My family had a fabulous 4 night stay at Tina’s place! There was plenty of space to lounge around and we all enjoyed the hot tub. We were a short drive to so many restaurants, farms, breweries and hiking spots. Tina responded immediately every time we asked a question. Would definitely stay here again!

Home in New Paltz

What guests are saying

Serene Country home 24 mi Mohawk ski area

4.94 out of 5 average rating, 32 reviews1 month ago

A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries

Home in New Milford

What guests are saying

La Sirena Beach Cottage

4.96 out of 5 average rating, 24 reviews4 days ago

House was just as it looked in the pictures - beautifully decorated. Has everything needed for a vacation. Comfortable, bright and cheerful. Back yard was private. House was fully stocked with what was needed along with beach supplies in the outdoor shed. Quick walk to the beach. Would easily rent again!

Home in Milford

What guests are saying

Seaside Paradise

5 out of 5 average rating, 5 reviews4 months ago

We stay 4 weeks at Jacqueline place, everything was great, did not have any problem. Place is exactly fit the advertising if not better and everything was clean and working. We find place and the area is so peaceful and quiet. Perfect location for someone just looking for rest in very beautiful neighborhood. Jacqueline was very responsive, easy to communicate, helpful and polite. I would definitely stay again and recommend for anyone needs a place feels like home away home.

Home in Milford

What guests are saying

State Forest Getaway

4.82 out of 5 average rating, 95 reviews1 week ago

Elena's house turned out to be a great vacation spot for us. It was conveniently located, very well maintained and guest friendly. Though rustic on the outside, the interior was completely redone, offering all modern amenities you might want. Kitchen was better equipped than most Airbnb's we've stayed at and was fun for us to cook in Without getting into much detail I'll just say that should we be in the area again we'll definitely return to this Airbnb and always recommend it to others

Home in Cornwall

What guests are saying

Newly built twin beach house within steps to beach

5 out of 5 average rating, 8 reviews8 months ago

We stayed here for a wedding at The Burr Mansion, which was extremely close to the house! The house was clean and updated. A few spots to walk to including a local bar. Just a walk to the beach. Bedrooms are all spacious and were very clean. Would definitely stay again.

Home in Fairfield

What guests are saying

Sleeps 16! Lake/Dock/Hot/Tub/SUP/Firepit

5 out of 5 average rating, 34 reviews5 days ago

Easily the best host I’ve came across, and I’ve rented many air bnbs in my life. House was immaculate. Brittany was accommodating, so easy to communicate with. My wife and I spent the weekend renting both of her properties hosting our bridal parties. She dropped offf two bottles of champagne for us. Couldn’t be more thankful. Great host!

Home in Brookfield

What guests are saying

Secluded Lakefront Chalet-Firepit&yard Dogfriendly

4.97 out of 5 average rating, 65 reviews1 month ago

What can I say? This is my 2nd time renting Wylda’s place in a matter of 3 weeks 😂 Absolutely LOVE this home. The most peaceful, beautiful and unique home/location in the area. I’m sure I’ll be back in the near future, and will continue to recommend this place to friends and family visiting the area.

Chalet in Carmel Hamlet

1 of 12 pages