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Condo vacation rentals in Windham

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Top-rated condo rentals in Windham

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Top guest favourite
The exterior of a historic two-story building is shown, featuring blue siding and white trim. A tall tree stands at the front, providing shade, while a decorative fence encloses the property. Steps lead up to the entrance, enhancing the welcoming appeal of the home.
Condo in Winthrop

The Day-Burrill-Wadsworth-La Voix House

The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. A historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two apartments and renovated).

4.98 out of 5 average rating, 120 reviews
Top guest favourite
The exterior of the condo features a classic brick façade with white trim. Steps lead up to the green front door adorned with a wreath. The walkway is lined with autumn leaves, and well-maintained shrubbery is visible alongside the building.
Condo in Manchester

Charming & Historic 2BR Oasis in Downtown Luxury

Step into the stylish and comfortable 2BR 1.5Bath condo in the heart of Manchester's historic downtown. Experience the city's rich history and visit numerous restaurants, shops, attractions, and landmarks, before retreating to our lovely oasis that will leave you in awe with its comfy design and rich amenity list that will satisfy your every need. ✔ 2 Comfortable Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Free Parking See more below!

4.99 out of 5 average rating, 207 reviews
Top guest favourite
Condo in Winthrop

Truly Oceanfront! Spacious Family Petfriendly Home

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

4.99 out of 5 average rating, 241 reviews
Guest favourite
A wooden staircase leads to a blue front door, framed by two hanging planters filled with vibrant flowers. A large, decorative white pot sits at the base, featuring a lush green plant surrounded by smaller potted plants, enhancing the entrance's welcoming appearance.
Condo in Chelmsford

The Art Experience

The Art House at the Ellison Building was built in 1878. This unit was renovated in 2004 and 2022. It is walking distance to both Freeman lake beach and also a boat launch for the Merrimack River. It's situated between Lowell and Nashua NH. 40 minute drive to Boston or Manchester. This 2 bedroom condo was renovated by artist/architect Daniel Forcier. All of the artwork hanging is for sale and Daniel has his art studio on site where classes are available for the complete art experience.

4.88 out of 5 average rating, 124 reviews
Top guest favourite
The modern kitchen features sleek stainless steel appliances and a spacious island with seating. Natural light fills the area from multiple windows, highlighting the granite countertops. A dining table sits within the open layout, creating an inviting space for meals.
Condo in Medford

Modern, Spacious, Top Floor Condo in A++ Location!

Modern, sunny second floor space with chef's kitchen! Newly renovated with gleaming hardwood floors, ample free parking, in-suite laundry, seventy five inch 4K smart TV, dining area, two generous bedrooms (one has king bed), separate living room, and sun porch. All this located in an exceptional location just steps from the Wellington Station Orange Line MBTA (the T) / Station Landing, Starbucks, Encore Boston, Life Time Sports Club, Planet Fitness, Restaurants, CVS, Assembly Row, & morer

4.96 out of 5 average rating, 113 reviews
Top guest favourite
Condo in Hampton Beach

Seacoast Getaway

Seacoast, NH’s popularity is well-earned, with museums, the finest restaurants, spas and shopping that blend perfectly with the Seacoast landscape. From our beautiful beaches and coastline combined with plentiful outdoor recreation, including fishing and whale watching, kite flying and more with Portsmouth, Rye, Exeter and Kittery Maine, all a short ride our beachfront condo has something for all. After a day of outdoor activity and exploring, come retire and rest in our place with a view.

4.98 out of 5 average rating, 353 reviews
Top guest favourite
A framed artwork features the silhouette of a raven against a shimmering gold background. The ornate frame adds a touch of elegance, enhancing the gothic decor of the space.
Condo in Salem

The Raven!

Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

4.96 out of 5 average rating, 120 reviews
Superhost
A spacious bedroom features two neatly made beds, one larger and one smaller, adorned with white bedding. A bedside table holds a lamp, and a window with light curtains allows natural light to enter, complemented by warm LED ceiling lights.
Condo in Waltham

Lovely one bedroom apartment condo, with parking

The whole group will enjoy easy access to everything from this centrally located place. Entire unit. In the heart of Waltham Large and comfortable one bedroom apartment in quite condominium style place. Great location 5 minutes walk to train or bus to Boston, 6 minutes walk to Moody street where all the restaurants and attractions are currently open. Also 7 minutes drive from Brandeis university or Bentley College . We are located near everything you would need to do in Waltham. The

4.83 out of 5 average rating, 150 reviews
Top guest favourite
Condo in Seabrook Beach

Welcome to the Beach Escape! Seabrook, NH

Come stay in the BEACH ESCAPE! Walk 1,000 feet to Seabrook Beach in New Hampshire. After a day at the beach, come back to relax on the balcony overlooking the marsh, watch the sunsets and fireworks. The condo sleeps up to 3-4 people with a full sized bed and full sleeper sofa, TV, WiFi, kitchenette, central AC, and 2 chairs. Walk to amazing restaurants steps away. Our goal is for you to have an amazing time on the New Hampshire Seacoast! We have a check in time of 2PM.

4.81 out of 5 average rating, 201 reviews
Top guest favourite
A modern living area features a black leather sofa paired with decorative pillows. A white area rug lies beneath a coffee table, complemented by an accent chair with a geometric pattern. Natural light filters through the two windows, creating a bright and inviting space.
Condo in Cambridge

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

A brand new spacious 3rd floor apartment over 1,000 sq ft centrally locate, near 2 subway stations/bus line, 4 grocery stores within 10 mins walk. The apt has a big kitchen, roof top deck and a huge yard. All brand new furnitures from Crate & Barrel, Pottery Barn and West Elm. Bed sheet sets from Crate & Barrel. NO Cleaning fee. We offer a great atmosphere, high quality amenities and cleanliness are utmost importance. Please read the reviews from prior guests.

4.93 out of 5 average rating, 900 reviews
Top guest favourite
The living area features a mix of comfortable seating, including a floral-patterned sofa and a plaid armchair. A round coffee table sits atop a light blue area rug, and large windows allow natural light to fill the space, enhancing the cozy ambiance.
Condo in Marblehead

Harbor View Suite

Harbor View Suite is a beautifully decorated two story Unit within a newly renovated Victorian house on the harbor located in Historic Old Town Marblehead, Massachusetts. This accommodation offers a rooftop terrace with panoramic views of the Harbor. Views of the harbor also from the kitchen deck. Perfect for families & friends.​ One dog allowed no cats please PLEASE note - parking on site is very tight small cars compact SUVs only

4.99 out of 5 average rating, 262 reviews
Guest favourite
Condo in Swampscott

Ocean View Coastal Retreat | Walk to Beach | Salem

Stay steps from the ocean in beautiful Swampscott, just a 3-minute walk to Fisherman’s Beach with front porch ocean views. Only 7 minutes to historic Salem, 5 minutes to the commuter rail, and about 30 minutes to Boston. Perfect for families, couples, girls trips, Salem visitors, and relaxing beach getaways looking to explore the North Shore and Boston while staying in a peaceful seaside neighborhood. Inhale the ocean air.

4.94 out of 5 average rating, 106 reviews

Popular amenities for Windham condo rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly condo rentals

Top guest favourite
A cozy living space features a queen bed with an orange throw blanket, complemented by natural light filtering through double windows. A mounted TV is positioned above a brick fireplace, while a comfortable sofa and a coffee table enhance the inviting layout.
Condo in Salem

The Green Suite, Private Parking Included

4.97 out of 5 average rating, 255 reviews
Top guest favourite
Condo in Hampton Beach

Adorable beach cottage with kitchen

4.94 out of 5 average rating, 113 reviews
Top guest favourite
A spacious living area features a modern gray sectional sofa with an accent pillow. Two windows provide natural light, framed by elegant window treatments. A flat-screen TV is mounted on the wall opposite a small coffee table set on a textured area rug, enhancing the inviting atmosphere.
Condo in Downtown Salem

Charter Street: Historic Charm, Modern Comfort

4.98 out of 5 average rating, 366 reviews
Top guest favourite
A dining area features a large black table surrounded by clear acrylic chairs, enhancing the spacious feel. A floral wallpaper adorns one wall, while light streams in through large windows. A chandelier adds an elegant touch to the room, complementing the hardwood flooring.
Condo in Swampscott

Modern Victorian close to Salem

4.99 out of 5 average rating, 133 reviews
Guest favourite
A tranquil bedroom features a spacious bed dressed in neutral linens, flanked by matching bedside tables with lamps. A work desk made of light wood is positioned against the wall, accompanied by a cozy blue pouf. Natural light is softly diffused through a window covered by light curtains.
Condo in Porter Square

Harvard / Porter Square Apartment, 2brm + sofabed

4.96 out of 5 average rating, 184 reviews
Guest favourite
The living area features two gray sofas positioned around a round wooden coffee table on a vibrant blue area rug. A cozy fireplace is situated against a striking red wall, complemented by a bookshelf filled with books. Natural light enters through a nearby window.
Condo in East Boston

Family Home + Near Downtown + Cool Backyard!

4.94 out of 5 average rating, 257 reviews
Guest favourite
A spacious living area features green walls and large windows allowing natural light. A plush blue sofa and armchair are arranged around a central coffee table on a patterned rug. A chair and television are positioned in one corner, enhancing the inviting ambiance.
Condo in Chelsea

Peaceful Chelsea Street |Top Floor Apt| Roof Deck|

4.82 out of 5 average rating, 119 reviews
Guest favourite
The image captures a view of the Atlantic Ocean, featuring gentle waves rolling towards the shore. A cloudy sky stretches above, while distant landforms can be seen along the horizon. Nearby buildings frame the scene, highlighting a coastal setting.
Condo in Hampton Beach

Oceanview Condo

4.9 out of 5 average rating, 140 reviews

Pet-friendly condo rentals

Guest favourite
A cozy living area features a dark sofa paired with decorative pillows, set atop a patterned area rug. A wooden coffee table occupies the center space, with a small plant adorning its surface. A doorway leads to a dining area visible in the background.
Condo in Salem

Beautiful Apartment in Nice Salem Area

4.89 out of 5 average rating, 300 reviews
Guest favourite
A well-lit bedroom features a spacious bed dressed in crisp white linens, flanked by small bedside tables with lamps. Large windows provide natural light and views of the surrounding area, while the soft blue walls create a calming ambiance.
Condo in South Boston

Penthouse 2 Beds /2 Baths luxury in South Boston

4.89 out of 5 average rating, 148 reviews
Guest favourite
A modern kitchen is showcased with light wood cabinetry and an expansive island featuring a white marble countertop. Pendant lights hang above, illuminating the space. The open layout leads to a cozy living area with a large sectional sofa, surrounded by windows that invite natural light.
Condo in East Boston

Luxury apt w/ sauna & deck | by airport, downtown

4.94 out of 5 average rating, 221 reviews
Top guest favourite
Condo in Gloucester

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN

4.96 out of 5 average rating, 202 reviews
Guest favourite
A bright living area is highlighted by a circular dining table surrounded by four chairs. A large round mirror above a white fireplace reflects the light. Warm wooden floors contrast with the cream walls, accentuated by subtle decor elements and natural light from nearby windows.
Condo in Boston

Condo in downtown Boston

4.88 out of 5 average rating, 171 reviews
Top guest favourite
A spacious living area is shown, featuring a light-colored sectional sofa, an accent chair, and a wooden coffee table. Natural light filters through large sliding doors, which open to a private deck. A soft area rug lies beneath the furniture, enhancing the cozy atmosphere.
Condo in South Boston

Boston Townhouse - 3BR/2.5BA - Seaport BCEC

4.95 out of 5 average rating, 133 reviews
Guest favourite
A well-appointed bedroom features a spacious bed with a light duvet and coordinating cushions. Two windows are dressed with patterned curtains, allowing natural light to fill the room. Artwork adorns the walls, complemented by a small desk with a potted plant and a chair.
Condo in North End

Gorgeous Huge Duplex 3 baths sleeps 6 Parking

4.77 out of 5 average rating, 265 reviews
Superhost
Condo in Somerville

Spacious, cozy home near Boston!

4.82 out of 5 average rating, 263 reviews

Condo rentals with a pool

Guest favourite
An aerial view of Hampton Beach highlights the proximity of the condo to the beach and nearby attractions. The coastline stretches out with sandy shores and a vibrant blue ocean. Nearby buildings and roadways are visible, providing a sense of the community and access to the area.
Condo in Hampton Beach

Steps from Beach | Pool | Parking | Large Deck

4.85 out of 5 average rating, 110 reviews
Top guest favourite
A bottle of 406 Co. Cellars wine rests on a wooden table beside two clear wine glasses. A decorative blue sign reading 'Hampton Beach' adds a touch of local charm to the setting. Soft lighting creates a warm ambiance.
Condo in Hampton Beach

406 Co. Seascape

4.97 out of 5 average rating, 100 reviews
Guest favourite
An open living area is visible, featuring a gray sofa, a patterned yellow armchair, and a dining table with six chairs. Large sliding glass doors provide access to a balcony, offering views of the outdoors. A kitchen counter and a coffee machine are also present.
Condo in Hampton

Serenity by the Sea

4.85 out of 5 average rating, 40 reviews
Top guest favourite
A view of the ocean is framed by large windows, displaying tranquil blue waters and sandy beaches. The image captures the shoreline and nearby buildings, offering a glimpse of the vibrant beach atmosphere.
Condo in Hampton Beach

Ocean View - Steps to the Beach!

4.96 out of 5 average rating, 55 reviews
Top guest favourite
The sleeping area features a queen Murphy bed with a soft white quilt and decorative pillows. Beside the bed, two lamps provide warm lighting, and a framed wall art piece in neutral tones is displayed above. Ample storage is available in stylish cabinetry.
Condo in Hampton Beach

Whale's Tale - Boutique Studio Condo with Pool

4.95 out of 5 average rating, 59 reviews
Guest favourite
Condo in Hampton Beach

Surfside - Boutique Studio Condo w/Pool

4.92 out of 5 average rating, 59 reviews
Guest favourite
A quaint bedroom features a queen size bed dressed with a floral patterned comforter. Two bedside lamps provide soft lighting, and a small refrigerator is positioned next to the bed. A television is mounted on the wall, and a colorful painting adds visual interest.
Condo in Hampton Beach

A Little Bit of Paradise | Steps From the Beach

4.98 out of 5 average rating, 50 reviews
Superhost
A newly renovated studio features a spacious bed with a leaf-patterned comforter. A wooden wardrobe stands against the wall, complemented by a mounted flat-screen TV. Soft lighting is provided by wall sconces, creating a cozy atmosphere. A seating area with a small table is visible.
Condo in Hampton

Hampton Beach Bailey's Resort

4.79 out of 5 average rating, 14 reviews

Destinations to explore