Windham vacation rentals
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Top-rated vacation rentals in Windham
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Home in Rockport
5 out of 5 average rating, 43 reviewsNew South End Home Quiet Lane To Old Garden Beach
Judy was a great host, very gracious and the place is beautiful. We loved walking around the area and would love to come back!
Apartment in Winthrop
4.96 out of 5 average rating, 301 reviewsCody's Place Boston Airport Pool/Beaches ParkFree
Frank and Kathy are THE BEST! The space was perfect—so clean and comfy. It was also private and easy to access. My favorite feature: the heater in the bathroom! The location is also 700 feet from my best friend, so I will be back!!! Truly, this has been my best AirBnB experience ever.
Cottage in Newbury
4.84 out of 5 average rating, 111 reviewsDesigner decorated-Sunset Bliss- Beach 3 min walk
Staying in this guest house was really great for me, my wife and our two small dogs. The front of the home overlooks are beautiful marsh. The area is very peaceful, and it's next-door to a quaint little park, and a few minutes walk to a private beach.
Apartment in Swampscott
4.89 out of 5 average rating, 104 reviewsOcean views, Large Deck, Grill, Kid/Dog Friendly
Perfect place to stay - sparkling clean, walking distance to the beach and to shops, gorgeous porch with ocean views & plenty of seating. Inside was comfy with high end finishes like marble, we loved using the gourmet 6 burner stove and large dining table. So many great things about this place, definitely recommend! Plus the host Ryan was super responsive & helpful.
Guest suite in Kittery Point
4.95 out of 5 average rating, 276 reviewsRomantic Spa By The Ocean. Hot Tub, Dining & Views
Kittery is adorable, and Maryalice’s place was very clean and comfortable. She was a great host and we’d stay again if we return!
Cottage in Newburyport
4.93 out of 5 average rating, 109 reviewsSunset Waterfront Privacy Beach
What a sweet little gem! Easy to find, private, serene and only 10 minutes from town which had many great restaurants and shopping! Kitchen was sunny and warm with the perfect hi-top table for puzzling. Living room & bed rooms were cozy & comfortable for reading & sleeping. Would love to return.
Home in Strafford
4.95 out of 5 average rating, 22 reviewsBow Lake Escape
Derek's house was very convenient for an extended Thanksgiving visit with our son, DIL and newborn grandson who live just a couple of miles away, and the kitchen was well equipped for the all the cooking we did during our stay. The house is very clean and Derek responded quickly to any questions we had. There was more than enough space for four adults and one child. Our other 11 year old grandson particularly liked the air hockey table and the downstairs TV. We also appreciated the ability to do laundry in-house.
Home in York
5 out of 5 average rating, 6 reviewsUltimate Panoramic Oceanfront
Stayed here with a group of friends for a weekend. Fantastic view! Functional spaces, with large kitchen for cooking. Would love to be here when its warmer to enjoy the outdoor spaces, but was also lovely during a snowstorm. Good communication with the host. Super easy check-in. Good for a large group.
Home in Hampton Beach
4.8 out of 5 average rating, 184 reviewsSteps to Beach | Fireplace | Pat's Porch
The place was perfect!! Well appointed, beachy theme, and very clean! I love the porch!! Chris kept in touch to make sure our stay was perfect!! We will definitely return!!
Home in Ogunquit
5 out of 5 average rating, 24 reviewsHoyts Ahoy
Christmas Magic! Our second stay at this lovely home! This time it was for Christmas and our wedding anniversary which is Christmas Eve. We couldn’t have been more delighted when we arrived and found the house decorated, inside and out, with beautiful Christmas decorations. Looked like a Hallmark movie, we loved it so much. The house was immaculately clean as it was before, hosted by truly lovely folks who are so kind and thoughtful. Great kitchen with everything you could think of to prepare meals. Comfortable beds, super lovely living room furniture, it’s just a wonderful space and very dog friendly (bowls etc provided, always a nice touch). This is our favourite airbnb by far and we absolutely recommend it!
Apartment in Downtown Manchester
4.8 out of 5 average rating, 5 reviewsLux Secure Access Parking & Elevator
First off, thank you to Norris and his team for letting us book a last minute eight day stay with them! As I was looking for a place, I wanted a private pet-friendly apartment that had laundry in-unit or in-building with a TV and free WiFi in a walkable area of Manchester with great restaurants and easy access to major highways for sightseeing in the city and beyond. Norris’s apartment checked off each and every box. My cat Prima loved bird and people watching from the windows within the unit. We had a great view of the city from those windows as well. Norris also provides a bellman’s cart to get your belongings into the apartment, which saved so much time and energy especially when you have a suitcase, litter box, cat food, cat accessories, and cat all in tow. We managed to get everything onto the cart, into the elevator, and upstairs in one go (thank goodness)! All in all: I could not ask for a better experience for our trip to Manchester and beyond.
Cottage in Wells
4.97 out of 5 average rating, 58 reviewsSuper cute one bedroom with hot tub and pool.
This was the second time my husband and I have stayed. Good location, cute bungalow, clean, close to many things. It makes for a nice long weekend get away. Joe was very proactive, when we booked he messaged right away. Sent door code etc. Highly recommend.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham vacation rentals
Other great vacation rentals in Windham
Apartment in Revere
4.81 out of 5 average rating, 108 reviewsHome away from home Beach,Logan,Encore, DownTown
I felt at home, the host was very kind, respectful and responsive. Great neighborhood, near to the Logan Airport, shopping centers and restaurants. The house is very clean and well arranged. It’s also very peaceful. We had so much fun staying there.
Apartment in Salisbury
5 out of 5 average rating, 36 reviewsNorth Shore Getaway for Adults
Tom and Penny set this place up perfect. There was nothing that they hadn't covered to make for a great stay. We really enjoyed the first class hospitality! Thank u! Patrick & Kristin
Home in York
4.94 out of 5 average rating, 31 reviewsMaine Oceanfront Cottage
Love the 180 degree view of the ocean! And the sounds of the waves! So close! We were a bit out of season so many restaurants were closed for the winter (we were there 11/7-8), but we found plenty! Ogunquit was still buzzing - so all was good. Love the place. The hosts did a lot with a small space - it was creative and cozy without feeling cramped. But again - the VIEW…
Home in Sandown
4.92 out of 5 average rating, 13 reviewsSunrise Beach Escape
What a great house to stay in! There was plenty of room for all 12 of us. And plenty for us to do. Fishing, hot tub, relaxing on the deck, walking down to the beach area, kayaking, paddle boating, playing board games, playing video games, pool, ping pong, air hockey, relaxing on the multiple couches watching tv or chatting, and enjoying meals around the table, which easily fit all 12 of us! The kitchen was well equipped - literally anything you could need, and lots of choices for the keurig. We only wish we could have stayed longer (we were there for a long weekend). We stayed in October so the weather was cool and it ended up raining for a lot of it, but we still enjoyed the beautiful view of the fall leaves on the pond. Would definitely recommend this house and we look forward to our next getaway on angle pond!
Home in Ogunquit
4.92 out of 5 average rating, 38 reviewsOgunquit Beach House - New Listing -Great Location
This house is everything and more. Amazing location, plenty of room, comfortable and clean. We had a blast. Close walk to town and beach. Aaron had plenty of beach chairs and a beach carrier for all your stuff. Plenty of space to park, grill, AC in all rooms. Was fantastic. Can’t wait to be back!
Condo in Salisbury
5 out of 5 average rating, 5 reviewsPanoramic penthouse beach view/water front.
We enjoyed our stay! Was close to local establishments and an easy driving distance to areas we came to visit! Super easy location to catch the train strait into Salem/Boston for the days we went there to sightsee! Diana was superb to work with and was always available for any questions we had.
Home in Northwood
5 out of 5 average rating, 10 reviewsDeja Blue Lake House
Overall was fantastic experience. The home was better prepared and stocked compared to other passed Air BnB experience. All in all family voted as one of the better Air BnB places to date.
Home in East Boston
4.86 out of 5 average rating, 92 reviewsCozy Oasis: Luxury & Modern Apt By Revere Beach
Lovely place. Everything you need. Nice views. Would for sure stay again.
Quick stats about vacation rentals in Windham
Total rentals
50 properties
Total number of reviews
3.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
Frequently Asked Questions
Where should I stay in Windham?
Make yourself at home in Windham by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in West Windham, and over 20 vacation rentals in Windham Depot.
Are there pet-friendly vacation rentals in Windham?
Four-legged friends are welcome in Windham. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Windham?
Yes! Work meets play with ease at over 20 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in cottage rentals in Windham?
Experience the best of Windham with our cottage rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly cottage rentals in Windham?
Windham has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Windham have wireless internet?
Absolutely! We offer over 20 house rentals with wireless internet in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Windham. Enjoy a tailored experience with all the comforts you desire.
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