Airbnb your place

Windham vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.

Top-rated vacation rentals in Windham

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Rockport

5 out of 5 average rating, 43 reviews

New South End Home Quiet Lane To Old Garden Beach

Newer furnished home, 1/2 mile walk to quaint Bearskin Neck with Rockport shops & galleries. Old Garden Beach 1/4 mile walk down a quiet unpaved lane. 3 BR/3 Bath home available for summer weekly vacations. Family friendly, 3 prkg spaces, 2 decks, new appliances (laundry, microwave & dishwasher), hardwood floors, new rugs & beds, full basement w/ pool table, fenced yard. Several beaches, hiking trails nearby or take a train to Salem, Newburyport, or Boston. Longer term winter rental available

Guest favorite

Apartment in Winthrop

4.96 out of 5 average rating, 301 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Guest favorite

Cottage in Newbury

4.84 out of 5 average rating, 111 reviews

Designer decorated-Sunset Bliss- Beach 3 min walk

Peaceful Plum Island cottage, renovated fall of 2018 and 2023 with New England coastal charm. Open floor plan and water views of the marsh, a short 3 minute walk to the beach. Watch the sun rise over the Atlantic and enjoy the spectacular sunset directly in front of the house for a nightly show. Walk the cottage for ice cream, Rip tide & the Sunset Club for cocktails and dinner. Beach, boating, fishing, wildlife sanctuary, and the historic downtown Newburyport all just 40 miles from Boston!

Guest favorite

Apartment in Swampscott

4.89 out of 5 average rating, 104 reviews

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

Guest favorite

Guest suite in Kittery Point

4.95 out of 5 average rating, 276 reviews

Romantic Spa By The Ocean. Hot Tub, Dining & Views

Just 10-minutes from charming Portsmouth! Enjoy the crystal-clean hot tub on your private patio. Feet-up pampering and special gifts throughout this adorable Maine coastal getaway. Drive into Portsmouth, or stay-in and pamper yourselves. Walk to the Kittery Point town wharf, historical sites, the Bistro and Wharf Restaurant, and catch views of the lighthouse and spectacular sunsets. 5-minute drive to a beach or world-class restaurants, 10-min to the famous Kittery Outlets.

Guest favorite

Cottage in Newburyport

4.93 out of 5 average rating, 109 reviews

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (heated June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.

Guest favorite

Home in Strafford

4.95 out of 5 average rating, 22 reviews

Bow Lake Escape

Newly renovated cottage nestled in the trees by beautiful Bow Lake! Sip your coffee on the deck listening to the loons & take the 1.6-mile drive or walk for a swim, paddle or float on the lake. Perfect for a relaxing getaway or outdoor enthusiasts. This 2BR/1.75BA stylish home sleeps 6 & offers modern amenities, seasonal lake views & convenient location near public boat launch & parking, restaurants, snowmobile trails & Antique Alley.

Guest favorite

Home in York

5 out of 5 average rating, 6 reviews

Ultimate Panoramic Oceanfront

Discover the charm of coastal Maine in this luxurious waterfront retreat located just under a half-mile from Long Sands Beach and close to Nubble Lighthouse. This stunning estate features breathtaking panoramic ocean views from almost every room. Observe surfers riding the waves and savor endless sunsets on the larges patios. This property offers the ultimate seaside lifestyle. Ready for the vacation you've always dreamed of!

Guest favorite

Home in Hampton Beach

4.8 out of 5 average rating, 184 reviews

Steps to Beach | Fireplace | Pat's Porch

Pat's Porch, the sister cottage of Lorraine's Landing and a professionally managed beach getaway - Just a 5-minute stroll from the sun-kissed shores and bustling boardwalk of Hampton Beach, this 3-bedroom, 1-bath abode boasts a queen master bedroom and newly updated kitchen. Relax on the expansive porch equipped with a picnic table, lounge chairs, and grill, or unwind indoors with fast wifi and a Samsung Smart TV.

Guest favorite

Home in Ogunquit

5 out of 5 average rating, 24 reviews

Hoyts Ahoy

Escape to the coastal beauty of Ogunquit, Maine, where your ideal vacation home awaits. This charming ranch-style 3-bedroom, 1.5-bathroom home has an appealing terrace and yard for gatherings, as well as a side patio with river and ocean views. The comfort and convenience are within steps of downtown Ogunquit, which offers everything from the beach, river, the famed Marginal Way, restaurants, and shops.

Superhost

Apartment in Downtown Manchester

4.8 out of 5 average rating, 5 reviews

Lux Secure Access Parking & Elevator

Stylish, safe, secure, clean and inviting with a very comfortable bed. The best value in hotel/home away alternative! Don't take our word, check our ratings and reviews. Dedicated, full time, on-site staff to insure your comfort and that your needs are attended to.

Guest favorite

Cottage in Wells

4.97 out of 5 average rating, 58 reviews

Super cute one bedroom with hot tub and pool.

This cottage is close to the beach, Rachel Carson wildlife preserve, loads of lobster serving restaurants. Hiking, biking, tubing, sunbathing or long walks are all nearby. Book now to take advantage of late summer and fall rates.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Windham vacation rentals

Gym
BBQ grill
Laptop-friendly workspace
Wifi
Air conditioning

Stay near Windham's top sights

Canobie Lake Park60 locals recommend
The Mall at Rockingham Park20 locals recommend
The Common Man11 locals recommend
Tuscan Kitchen11 locals recommend
Tuscan Village Marketplace8 locals recommend
Enterprise Rent-A-Car8 locals recommend

Other great vacation rentals in Windham

Superhost

Apartment in Revere

4.81 out of 5 average rating, 108 reviews

Home away from home Beach,Logan,Encore, DownTown

Guest favorite

Apartment in Salisbury

5 out of 5 average rating, 36 reviews

North Shore Getaway for Adults

Superhost

Home in York

4.94 out of 5 average rating, 31 reviews

Maine Oceanfront Cottage

Guest favorite

Home in Sandown

4.92 out of 5 average rating, 13 reviews

Sunrise Beach Escape

Guest favorite

Home in Ogunquit

4.92 out of 5 average rating, 38 reviews

Ogunquit Beach House - New Listing -Great Location

Guest favorite

Condo in Salisbury

5 out of 5 average rating, 5 reviews

Panoramic penthouse beach view/water front.

Guest favorite

Home in Northwood

5 out of 5 average rating, 10 reviews

Deja Blue Lake House

Superhost

Home in East Boston

4.86 out of 5 average rating, 92 reviews

Cozy Oasis: Luxury & Modern Apt By Revere Beach

Show all

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.

Destinations to explore