House vacation rentals in Windham

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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 stars2 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 stars1 month 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 stars3 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 Ski & Swim Escape

AmandaRating, 5 stars2 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, 148 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

NandaRating, 5 stars2 months ago
Brad is a wonderful host. He checked in to make sure I was happy with everything and was quick to respond to my messages before I arrived. His house is very comfortable with everything my family needed for a relaxing stay. The view of the golf course from the bedroom was a nice plus. We felt right at home. Highly recommend!
Superhost

Home in South Berwick

4.7 out of 5 average rating, 10 reviews

Coastal Home Heated Pool, Hot Tub, Outdoor Kitchen

JuliaRating, 5 stars5 months ago
The place was fantastic! Looked just as pictured/described. We were a group of 8 adults and 4 kids and were very comfortable. The pool and hot tub were great, clean, and heated as promised. It felt private even though there were other units on site. The space is large and winding - a kids hide and seek dream :) lots of gathering spaces to hang out. John was super responsive and helpful. Thanks!!
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

4.9 out of 5 average rating, 156 reviews

Sanctum by the Lake

IsabelaRating, 5 stars1 day ago
Very cozy, clean and pleasant environment… I would definitely come back again! Amazing experience!! Thank you so much.
Guest favorite
The serene lake is framed by trees, reflecting the soft colors of the sunset sky. Gentle ripples disturb the water's surface, creating a tranquil atmosphere. In the distance, the silhouettes of trees and properties are visible along the shore, enhancing the peaceful landscape.

Home in Derry

4.83 out of 5 average rating, 134 reviews

Beautiful Lakefront Vacation

BobRating, 5 stars5 months ago
Donna is fantastic and if your looking for a charming New England spot this is it! We Are very satisfied with this home.

Weekly house rentals

Guest favorite

Home in Ogunquit

4.95 out of 5 average rating, 73 reviews

Opening late April !

MaryRating, 5 stars4 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 wide sandy beach extends towards the horizon, reflecting the calm ocean water. Various beachside buildings and accommodations line the shore, creating a peaceful coastal atmosphere. The sky is overcast, contributing to a serene, muted color palette.

Home in Salisbury

4.87 out of 5 average rating, 202 reviews

Spacious waterfront free parking &Wi-fi

MelissaRating, 5 stars1 week ago
Diana was very warm, responsive, and helpful throughout every aspect of our stay. Her home is located right across from Salisbury Beach with easy walking access to the water. The home is clean and spacious and has everything you could want or need for a comfortable stay.
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 stars5 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.
Guest favorite

Home in Shrewsbury

5 out of 5 average rating, 10 reviews

Lake "Island"

JamesonRating, 5 stars1 month ago
We rang in the New Year with a peaceful get away at the Martin's gorgeous A-frame. The hosts were extreme communicative and helpful—they even worked with us to bring a sauna onto a property. This is a wonderful getaway just 50 minutes from Boston that I will absolutely be returning to.
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 stars2 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, 121 reviews

Mid-Century Modern in Historic Lexington

WilliamRating, 5 stars3 months ago
Samuel's place is truly beautiful! What a setting in the woods! Everything was great.
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, 52 reviews

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

AndrewRating, 5 stars2 months ago
We had a nice, quick Thanksgiving stay. Kimberly’s place was beautiful and comfortable.
Guest favorite
A tree in bloom stands in front of a two-story home with light-colored siding, situated on a serene dead-end street. A driveway reveals a vehicle parked near the entrance, providing a welcoming view of the property.

Home in Old Orchard Beach

4.87 out of 5 average rating, 159 reviews

Clean, private 3 bedroom home 1 mile from beach

ThomasRating, 5 stars3 months ago
Great spot with a lot of space you never feel like you are on top of each other. Gas station and restaurants within a 1 min drive. Grocery store 5 min drive.

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

4.94 out of 5 average rating, 18 reviews

Beach House on a Private Beach!

LauraRating, 5 stars5 months ago
Gaby’s place was an absolute gem. What gorgeous views! Our family really enjoyed the beach and paddling about the harbor as well. The house was very clean. Gaby was friendly and responsive. We plan to return in the future! Thank you Gaby!
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, 333 reviews

Beautiful, Peaceful, Maine Getaway House

JulianRating, 5 stars4 days ago
Everything was perfect at Kathy's place! We found the peace we we're looking for!! Thanks you very much!!
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 stars4 days 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!
Superhost
A living room is presented with decorative elements, including a fireplace with a floral arrangement and a classic portrait. Comfortable seating is provided by various chairs and a plush sofa, while a wooden coffee table occupies the center space. Soft natural light enters through the window.

Home in Wellesley

4.76 out of 5 average rating, 17 reviews

Vintage home with modern conveniences

Vivian And RobertRating, 5 stars2 months ago
Our family really enjoyed our second stay at Louise’s lovely house. The house is spacious, well furnished, comfortable and well situated. Louise is a terrific host — very responsive, thoughtful and friendly. We love staying here and hope to do so again.
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, 166 reviews

3 bedroom impeccable private home, quiet street

AnnieRating, 5 stars2 months ago
Comfortable, clean, organized with lots of amenities. Easy check in. Great beds. Spacious. Quick, friendly, helpful communication with Smaranda. It's close to family so would stay here again!
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 stars5 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 exterior of a three-story townhouse is showcased, featuring a dark blue facade and a welcoming front porch. A paved parking area with clearly marked lines accommodates multiple vehicles. Surrounding greenery and fencing provide a sense of privacy and tranquility.

Home in Quincy

4.88 out of 5 average rating, 145 reviews

284 - Entire House with Big Patio

DougRating, 5 stars3 weeks ago
Perfect home for a family. Tons of space for everyone. We will definitely stay here again when in town.
Guest favorite

Home in Manchester

4.83 out of 5 average rating, 24 reviews

North End Family Oasis

EdwinRating, 5 stars1 month ago
We had the most wonderful stay at Nancy's home! The house was beautifully maintained, spacious, and had everything we needed for our family. The bedrooms were cozy, and the living area was perfect for relaxing together. We especially enjoyed the peaceful neighborhood. Our stay was brief, but memorable. I would absolutely recommend this home to anyone visiting the area.

Quick stats about house rentals in Windham

  • Total rentals

    20 properties

  • Total number of reviews

    1.3K 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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