House vacation rentals in Windham

Find and book unique houses on Airbnb

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Popular amenities for Windham house rentals

House rentals with a pool

Guest favorite
The entrance to the home features a welcoming porch adorned with a hanging planter and a white chair. Vibrant tulips and various flowers create a colorful border along the stone pathway, leading toward the front door framed by classic shutters.
Home in North Andover
4.94 out of 5 average rating, 152 reviews

Nana-tucket Inn

JeremyRating, 5 stars5 months ago
We had an absolutely wonderful experience staying at this Airbnb! The home was impeccably clean, cozy, and well-stocked with everything we could possibly need. The host's attention to detail was evident in every corner, from the kids' toys to the thoughtful touches like snacks, coffee, and local guidebooks. The location was perfect—peaceful and quiet but still close to shops and restaurants. I especially loved relaxing in front of the fire and enjoying the serene surroundings. The host was incredibly responsive and went above and beyond to ensure our stay was seamless, offering great tips about the area and checking in (without being intrusive). I highly recommend this spot to anyone visiting North Andover or the greater Boston area.
Guest favorite
A modern New Englander home is nestled among lush greenery, featuring a wraparound porch and a red front door. Solar panels are installed on the roof. A driveway leads to the entrance, while basketball equipment is positioned near the side of the house.
Home in Kittery
4.95 out of 5 average rating, 40 reviews

Fantastic Kittery Home with Pool

BarbaraRating, 5 stars3 months ago
The house was perfect for my family and I- plenty of open space for the kids to play and a great yard- even in December with cold weather the kids loved the play gym outside!! The location was amazing with lots of things to do within a few minutes and the food scene was great. Thanks to Ned for a spotless home and great amenities!! We can’t wait to come back in the summer to use the pool!!
Guest favorite
A private deck features a heated hot tub and two lounge chairs positioned on an outdoor rug. A white privacy fence surrounds the area, enhancing the tranquil setting. Sunlight creates a bright atmosphere, reflecting off the water's surface in the hot tub.
Home in Hampton
5 out of 5 average rating, 37 reviews

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

VeronicaRating, 5 stars6 months ago
LOVED LOVED! My friends and I all agreed that this house looks just like the pictures for once! Very nice unexpected touches/surprises. House had everything you could really need! I believe the host could get away with charging more in my opinion! I hope to come back in the future.
Superhost
A sandy beach area is visible, surrounded by several red adirondack chairs arranged around a small fire pit. A black lounge chair sits nearby. A pontoon boat is docked on the water, with a paddle board lying on the grass beside the seating area.
Home in Barnstead
4.84 out of 5 average rating, 101 reviews

Locke Lake Waterfront Escape

AmandaRating, 5 stars5 months ago
Me and my family had an awesome stay. The house was great with lots of space and places to sleep. We were 8 ppl and there was more than enough room. Garage/game room was awesome I just wish it was insulated with some heat we had to wear our coats to be comfortable, of course the weather was 26F so it was expected. The rest of the house was warm and cozy. I would love to rent this same house in the summer it must be amazing with the view of the lake. One more thing is although there are 2 bathrooms its more like 1 because the second bathroom upstairs has a little door that leads to the room with the 4 beds so the other people not staying in that room didn’t use that bathroom to not get walked in on unexpectedly. Overall I still gave this place 5 stars and it’s one of the best places I’ve stayed and the host is very responsive and accommodating.
Guest favorite
An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.
Home in Hopkinton
4.95 out of 5 average rating, 153 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars1 week ago
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.
Superhost
A spacious living room features large windows allowing natural light. Comfortable seating is arranged around a coffee table, with a cozy area rug anchoring the space. A television is mounted on the wall, and a bookshelf adds a touch of decor. Sliding doors lead to an outdoor balcony.
Home in Wells
4.67 out of 5 average rating, 12 reviews

Stunning Beach House with an in-ground pool!

StephanieRating, 5 stars10 months ago
we stayed in this house years ago so we knew what to expect. again, it delivered! Coastline Vacation Rental was very well organized with reminders and easily reached by text. much more so than other rental companies. this was so appreciated. the kitchen well stocked for cooking and everything clean and ready to go. beds comfortable and we love the space for family to spread out or get together to play pingpong. highly recommend this property.
Superhost
A bright pool area is depicted with a crisp blue swimming pool surrounded by a spacious concrete deck. Lounge chairs are arranged near the pool, and a small building stands nearby, accompanied by trees and a well-maintained lawn, suggesting a serene outdoor environment.
Home in Bedford
4.67 out of 5 average rating, 33 reviews

Bedford Retreat: pool, fenced yard.

GailRating, 5 stars7 months ago
Host was friendly and helpful. House is located in an area close to a great grocery store and lots of shopping. It,s also not far from the mountains for those who want to leaf peep in the fall. The house is cozy and has everything you could want, just have to bring yourselves.
Guest favorite
A spacious living room features a large sectional couch and an accent chair, both positioned on a patterned area rug. A wall-mounted TV is visible, with light streaming through the windows, highlighting the natural wood flooring and airy design.
Home in Derry
4.91 out of 5 average rating, 175 reviews

Sanctum by the Lake

AmandaRating, 5 stars4 days ago
My friends and I went for a weekend trip and had such a great time. Steve responded quickly to messages and made it clear that if we had any questions, to reach out at any time. Such a great place!

Weekly house rentals

Guest favorite
Home in Ogunquit
4.95 out of 5 average rating, 73 reviews

Opening May 16th

MaryRating, 5 stars6 months ago
Accomodations exactly as shown in pictures. Kitchen is definitely well equipped with all of the essentials and more. Ice cream shop right next door is great and The Lobster Pound on the other side is excellent. You can walk to shops and restaurants downtown but we had no problem finding parking in the evening so we could enjoy the awesome restaurants.
Guest favorite
A view through the window showcases the ocean and beach, framed by a stone column and a decorative railing. Comfortable seating in teal decor is visible, inviting relaxation while enjoying the coastal scenery.
Home in Salisbury
4.88 out of 5 average rating, 211 reviews

Spacious waterfront free parking &Wi-fi

AnthonyRating, 5 stars5 days ago
Had a wonderful stay here, perfect location and was able to enjoy the sounds of the ocean the entire time. Would definitely recommend staying here and I’d look forward to being here again in the future. Thank you so much!
Top guest favorite
The exterior of the cottage is visible, featuring light gray siding and multiple windows with white trim. A vibrant display of pink flowers is situated in the foreground, providing a colorful contrast to the structure.
Home in Hampton Beach
4.96 out of 5 average rating, 273 reviews

2 Bedroom Beach Bungalow, Steps from the Beach!

JillRating, 5 stars4 days ago
The location was perfect. We selected the cottage because of the proximity to Hampton State Park Beach which was, as is described in the posting, only a few steps away. The cottage is also quite close to the boardwalk. It would be great for a group that wanted the best of both - quiet neighborhood and accessible to eating and entertainment. The cottage was clean and cozy, just right for our party of four, and had available many little items travers might need or left behind at home. Sharon was helpful and very responsive.
Superhost
A weathered barn with a cupola is framed by greenery, overlooking the ocean in the distance. Soft pastel colors of the sunset wash over the sky, enhancing the serene landscape. The spacious yard is visible in the foreground, providing a tranquil outdoor setting.
Home in Rockport
5 out of 5 average rating, 3 reviews

Rockport Vacation Home, ocean views, 2 bed/1 bath

MiklósRating, 5 stars7 months ago
Great House with a big backyard and deck. The home is in a great location with views of the ocean. Sandy’s place was perfect for my group and I . Easy parking for 3 sedans. Piano was a nice touch and was perfectly in tune for such a humid summer.
Superhost
A charming ranch-style home is showcased with a blue front door and classic window shutters. Two light-colored chairs are placed on the manicured lawn, surrounded by vibrant pink flowers. The entrance is framed by white railings and a well-maintained pathway.
Home in Seabrook Beach
4.76 out of 5 average rating, 82 reviews

Beach Bums' House - Perfect for Families & Friends

HollyRating, 5 stars5 months ago
This is an older ranch with a spacious kitchen and super comfortable beds. A beautiful beach is steps down the road. It is the first house off the highway, so you may hear traffic noise. There is a dehumidifier, which you will need to turn to the highest setting. The host is friendly and very responsive.
Guest favorite
A mid-century house is positioned among lush greenery, showcasing a modern exterior in muted tones. A paved driveway leads up to the entrance, framed by a natural landscape of trees and grass, creating a serene and inviting outdoor environment.
Home in Lexington
4.92 out of 5 average rating, 119 reviews

Mid-Century Modern in Historic Lexington

MichaelRating, 5 stars3 weeks ago
Great place for our coaches to meet up and sleep after a full day of coaching in Boston area. Very comfortable space. Highly recommend this home.
Top guest favorite
The exterior of a cottage is displayed, featuring a charming blue facade and a welcoming porch. White Adirondack chairs are positioned in the foreground, surrounded by a well-kept garden with colorful flowers. A shaded area is visible in the background with a sun umbrella.
Home in Biddeford
4.98 out of 5 average rating, 53 reviews

Hills Beach UNE 3-4 brs oceanview 50 steps 2 beach

LewisRating, 5 stars3 months ago
Fabulous; lovely place, close to the beach, good internet, nice amenities.
Superhost
A spacious outdoor seating area is framed by a wooden pergola, with soft lights enhancing the ambiance. A circular fire pit sits at the center, surrounded by a curved sectional couch and additional chairs, offering a comfortable space for gathering near the water.
Home in Laconia
4.92 out of 5 average rating, 239 reviews

Waterfront with Game Room Pergola Firepit Downtown

AmberRating, 5 stars2 months ago
The bed was so comfy! We had so much fun with the game room. It was such a cool addition

Private house rentals

Guest favorite
The living room features a light and airy design, with large windows providing ocean views. A comfortable sectional sofa and two armchairs are positioned around a rustic wooden coffee table. Bright decor elements and a ceiling fan enhance the inviting space.
Home in Annisquam
4.96 out of 5 average rating, 24 reviews

Beach House on a Private Beach!

StephanieRating, 5 stars4 days ago
Gabriela's beach house was so beautiful and the views were unbelievable! Right on the beach and the house had plenty of space for my family and I. She was very responsive as well! I would definitely stay again!
Top guest favorite
A serene snowfall blankets the landscape, with a quaint house visible in the background. The house features a front porch and is surrounded by tall trees. A smooth, snowy path leads up to the entrance, highlighting the peaceful, winter setting.
Home in Lebanon
4.97 out of 5 average rating, 352 reviews

Beautiful, Peaceful, Maine Getaway House

NellyRating, 5 stars4 days ago
My fiancé and I recently had the pleasure of staying at a lovely dog-friendly house in Lebanon, Maine, and I can't recommend it enough! From the moment we arrived, we felt right at home. The property was spacious, clean, and beautifully decorated, making it the perfect retreat for both humans and our furry friends. The backyard was a highlight, providing plenty of space for our dogs to run around and play. The location was also fantastic, with easy access to nearby walking trails and dog-friendly things to do in the area. Overall, this Airbnb exceeded our expectations, and we can't wait to return for another stay! Highly recommend it for anyone looking to enjoy a getaway with their pet!
Guest favorite
A private driveway leads to a modern house with a red exterior and a silos-style structure. The property is framed by green trees and an expansive lawn, creating a welcoming entrance. Stone pillars with lanterns mark the beginning of the path.
Home in Wells
4.99 out of 5 average rating, 78 reviews

Beach Home w/ Exclusive privacy in Southern Maine

JordanRating, 5 stars2 months ago
We had a wonderful time in Wells! An absolutely beautiful home with every amenity! Sharon was responsive, kind, and flexible with our stay. We enjoyed cooking and watching the Super Bowl in the amazing home theater! Do not miss out on this fantastic listing!
Guest favorite
Home in Shrewsbury
5 out of 5 average rating, 12 reviews

Lake "Island" near Boston

OliviaRating, 5 stars1 month ago
Really cool place! Very peaceful and quiet!
Superhost
A tranquil bedroom features a spacious bed with floral-patterned bedding. Two nightstands with matching lamps are positioned on either side. Natural light filters through sheer curtains, complementing the soft wall color and enhancing the serene ambiance of the room.
Home in Canton
4.83 out of 5 average rating, 170 reviews

3 bedroom impeccable private home, quiet street

PhilipRating, 5 stars4 days ago
We found the perfect spot to visit Trillium for the Boston Hot Sauce Party! The guys from Full Slice Podcast and Table Top Trio say thank you and hope to come back next year!
Top guest favorite
A light blue exterior of the building is presented, featuring white shutters and multiple windows. A wooden deck with steps leads to the entrance. The surrounding area includes white gravel, decorative items, and a small bench for relaxation.
Home in Wells
4.94 out of 5 average rating, 72 reviews

Beautiful House to Relax & Enjoy the Quiet!

NinoRating, 5 stars7 months ago
We had a wonderful stay. The house was very nice and all accommodations were met and exceeded. We cooked dinner in the kitchen two of the nights we were there and found everything we needed very easily. Everything was very clean and well taken care of, yet felt extremely homey and welcoming! The fire pit and outdoor bar were an amazing benefit, the whole back/front yards and patios in general were amazing. It’s safe to say we truly enjoyed our time in this home and will be checking here first next time we come! Highly recommended stay!
Guest favorite
The living room is designed for relaxation with a comfortable sofa and a flat-screen TV. Natural light fills the space through large windows, illuminating the hardwood flooring. A center coffee table enhances the inviting atmosphere, encouraging gatherings after a day of exploring.
Home in Quincy
4.88 out of 5 average rating, 147 reviews

284 - 5BR Boston | Peaceful Stay near Clipper

KathyRating, 5 stars1 month ago
Quaint, clean and very spacious home. We were a party of 10 and had plenty of room. Jenny was very helpful from start to finish.
Guest favorite
A modern kitchen features sleek gray cabinets and a spacious island with four bar stools. New appliances, including a stainless-steel refrigerator and stove, complement the elegant marble countertop. Natural light filters through the window, enhancing the clean lines and organized layout of the space.
Home in Manchester
4.87 out of 5 average rating, 30 reviews

North End Family Oasis

JamisRating, 5 stars4 days ago
The space was perfect for our family great away. The huge kitchen, private bedrooms and quiet space allowed us to relax and still have family time together. The house was immaculate. Would book this space again!

Quick stats about house rentals in Windham

  • Total rentals

    20 properties

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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