Holiday rentals with outdoor seating in Roxbury

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Roxbury

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite

Tent in Poughquag

4.85 out of 5 average rating, 13 reviews

Maybrook Farm "The Ridge"

Soaring view of Hudson Valley from tent on 100 Acre Farm - Direct Access to Empire Rail Trail - Fishing at our Pond! Walk to Appalachian Trail! Enjoy the stars at night and beauty of hills and valley from your canvas tent equipped with bed. Drive up or come by bike to private entrance to the farm from the Empire Rail Trail with a locked gate. The pond has a dock, there is a seasonal babbling brook, walking trails, wildlife. Fire pit, picnic table, outhouse bathroom. Rustic, simple, beautiful!

Top Guest favourite

Chalet in Poughquag

4.97 out of 5 average rating, 74 reviews

The Lookout

Massive 4,000 sq foot chalet on more than seven acres. Only 90 minutes from NYC, with incredible mountain views and stunning sunsets. Floor-to-ceiling stone fireplace, outdoor firepit, 8 person hot tub, and gas grill for use. Private hiking trail on property. Close proximity to all of Hudson Valley's best golf courses, breweries, wineries, hiking trails, parks, and ski resorts. Easy drive to historic Beacon, Cold Spring, Rhinebeck, Pawling, and New Paltz, and only minutes away from Metro North.

Guest favourite

Home in East Haven

4.97 out of 5 average rating, 149 reviews

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

Top Guest favourite

Holiday home in Warren

4.98 out of 5 average rating, 165 reviews

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Top Guest favourite

Cottage in Southwick

4.98 out of 5 average rating, 106 reviews

4 Kayaks Fire Pit & Lake Views from Hot Tub

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for 2 families. (4 adults w/4 kids or 6 adults) Minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

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.

Superhost

Chalet in Goshen

4.89 out of 5 average rating, 142 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.

Top Guest favourite

Cottage in South Salem

5 out of 5 average rating, 103 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.

Top Guest favourite

Guesthouse in Bethel

5 out of 5 average rating, 16 reviews

Tranquil getaway cottage in charming neighborhood

Escape the city bustle and unwind in the tranquility of The Red Cedar Cottage nestled between Bethel and Newtown, just a short drive from Danbury, CT. Tucked away in a peaceful neighborhood, this fully renovated cottage offers a serene getaway for couples seeking relaxation. Unwind in style on a high-end king-sized mattress in a whimsically curated space designed to rejuvenate your senses. Discover the Red Cedar Cottage and immerse yourself in a tranquil escape from the ordinary.

Top Guest favourite

Home in Milford

5 out of 5 average rating, 102 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach, Silver Sands, dining, shops & more, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Guest favourite

Cottage in Plymouth

4.94 out of 5 average rating, 115 reviews

Lakefront Cozy Oasis 2BR w/ stunning sunset views

It’s the Lakefront Paradise you’ve been searching for: Escape to Cozy Oasis where peaceful waters meet modern comfort! Wake to stunning views, spend the day kayaking around the lake, and unwind with breathtaking sunsets from your private deck. This pet-friendly retreat offers high-speed WiFi for remote work, fully equipped kitchen for home-cooked meals, and cozy entertainment spaces. Perfect for romantic getaways or family adventures - your serene lakeside escape awaits

Top Guest favourite

Tent in Southbury

5 out of 5 average rating, 16 reviews

Romantic Botanical Glamping

A spiritual respite for relaxation and mental wellbeing. The perfect relaxing Romantic Botanical Glamping Spiritual Garden Retreat Getaway, off the beaten track but close to civilization with a rustic romantic flair. Pool, gardens, seasonal vegetables & fruit & Fall Colors. Local activities within minutes. Recline by the pool or gardens, or at the plush upscale movie theater in town. Antique trail, wine trail, breweries and distilleries. 24+ hiking areas.