
Holiday rentals with outdoor seating in Windham
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Windham
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Boulder House - Extraordinary Luxury in the Woods!
From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Air Bee-n-Bee Hive-Unique Themed Stay, Coffee bar
Plan a unique and memorable stay at the Hive, a bee-themed apartment in a Boston suburb 21.1 miles from the city. Delight in the charming honeybee-inspired décor. Relax on the patio and enjoy the nearby chickens and geese – and especially their fresh eggs. You’ll love the entertainment options – 100s of free movies plus cable TV and access to streaming channels. Everything you need is here, from a full kitchen with a coffee bar to EV charger. Got work? A workspace and super-fast Wi-Fi await you.

The Birch Suite: Large, Cozy NH Themed Apartment
Our home and attached apartment is tucked away in a quiet neighborhood in southern NH, just minutes from major N/S highway Route 93. We are thrilled to offer our New Hampshire-themed apartment to individuals, couples and families. Each room is decorated to represent the most interesting aspects of our state: the purple lilac bathroom, the maple bedroom, the white birch living room and a large second bedroom/playroom we call "the state room" - a fun, educational room of all things New Hampshire.

One Level 2 bedroom suite on private cul-de-sac
Welcome to The Sama's Airbnb. Windham was recently named the #1 town in the Granite State. Here, you will enjoy a complete newly renovated private one level 2 bedroom suite complete with full kitchen, cozy living room, 40 inch LED TV with all channels, wifi, washer and dryer, new tennis court, 1/2 basketball court and pickleball, beautifully landscaped grounds on a private cul de sac yet close to Boston, beaches, mountains, shopping, great restaurants, Searles Castle, Canobie, & Tuscan Village.

Haven by the Lake
Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the hot tub, loft room, and lake access, The Haven by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

Cottage beside a waterfall
Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

Peaceful Mill on the Water - Home Away from Home
Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated workspace.

Accessory Apt on Wooded Property
Forget your worries in this spacious and serene space. Guest House/Over Garage Apartment tucked away on 6 acres. Centrally locataed in the seacoast region of New Hampshire. Close to mountains, beaches, hiking trails, lakes, & more. 15 minutes to Exeter, 30 minutes to North Hampton/Hampton Beach, 35 minutes to Southern Maine and Portsmouth, NH, 40 minutes to Manchester Boston Regional Airport, and 1 hour to Downtown Boston yet still tucked away in your own private retreat in the woods.

Downtown Derry, Studio Apartment
Cozy up during your next trip to southern NH! Built in 1910, the home has been completely renovated. The Studio is a combination of elegance and comfort from the walls of windows that flood the space with light and scenic conservation/golf course views to the spacious backyard that is perfect for a peaceful escape. It is 5 minutes from i-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Downtown Derry, Loft Apartment
Cozy up during your next trip to southern NH! Built in 1910, the home has been completely renovated. The Loft is a combination of elegance and comfort from the walls of windows that flood the space with light and scenic conservation/golf course views to the spacious backyard that is perfect for a peaceful escape. It is 5 minutes from i-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Newly renovated, spacious, clean, 3 bedroom home.
Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

*Beachfront* Vintage Coastal Cottage - Relaxation
It's always about the view and this place will leave you feeling energized and calm. Situated on premium beachfront property, this single family home has luxurious amenities like super plush towels, organic cotton bedding and touches to make your getaway feel that much Take a virtual tour here: https://bit.ly/3vK5F0G We've outfitted it with an extra screen and a setup to get you up and running. Google home and Sonos systems bring this 100 year old beauty into this century.
Popular amenities for outdoor seating rentals in Windham
House rentals with outdoor seating

Nana-tucket Inn

Great for Families Modern Farmhouse Near Shopping

A water view slice of heaven at Pepperrell Cove

Stone Cottage with meadow view

Luxurious Oceanfront Property

Residential home ▪ Billerica ▪ quiet, clean & cozy

Idyllic Small-Town Stay (2 Bed)

Spacious Private Loft on Main Street (3rd FL)
Apartment rentals with outdoor seating

Hipster Basecamp | fireplace • views • parking

Modern Apartment - Easy Commute to Salem/Boston

Couples Retreat - Apt in Charming Colonial Home

Unit 2~Garden Getaway Close to Beach & Downtown

Your Cozy 1 BR Apt & Relaxing Retreat

Villa Ricci

Warm home in Lexington, walk to town, nature trail

City Loft | Group Getaway | King Downtown Location
Apartment rentals with outdoor seating

My Place - 2 Bedroom Condo with Parking

Newly Renovated Victorian close to Salem

Sunny Beach Studio Condo with Sunset View

Cozy Entire Unit Condo close to UMASS Lowell

Top Floor Condo ~ Steps from the Water & Downtown

The Salem Porch House

Samuel Tucker House - Downtown Luxury 2 Bed Condo

New Super Modern 2 bed in Waltham
Quick stats about holiday rentals with outdoor seating in Windham

Total holiday rentals
Explore 10 holiday rentals in Windham

Nightly prices starting at
Windham holiday rentals start at $104 SGD per night before taxes and fees

Verified guest reviews
Over 1,050 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Windham holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Windham rentals

4.9 Average rating
Windham stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with outdoor seating Rockingham County
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- Hampton Beach
- Ogunquit Beach
- Fenway Park
- Boston Common
- Wells Beach
- TD Garden
- Harvard University
- Revere Beach
- Lynn Beach
- York Harbor Beach
- Monadnock State Park
- New England Aquarium
- Long Sands Beach
- Good Harbor Beach
- Freedom Trail
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- Quincy Market
- Rye North Beach
- North Hampton Beach
- Prudential Center