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Condo holiday rentals in Windham

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Top-rated condo rentals in Windham

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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, 208 reviews
Guest favourite
A stylish living area features a dark leather sofa positioned near a modern glass coffee table. A flat-screen television sits on a black media unit. Two windows provide natural light and a dining table is set for four, enhancing the open and functional layout.
Condo in Dracut

Cozy Entire Unit Condo close to UMASS Lowell

My place is close to restaurants, UMASS. Lowell, and almost anything you need. You’ll love my place because instead of having a spare room in someone's house, you get an entire condo and privacy available to you (owner lives in separate unit). The unit includes basic amenities included (toiletries, bedding etc). In addition, the unit comes with a PlayStation 4 for the kids (or the husband/boyfriend) to keep them busy :) My place is good for couples, solo adventurers, and business travelers.

4.86 out of 5 average rating, 122 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, 126 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, 359 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, 125 reviews
Top 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!

Welcome to our family home. It's convenient, comfortable, safe, and close to downtown Boston! We have a backyard and open space with a beautiful deck. It's a great place to spend time and enjoy a peaceful outdoor setting in the city. Located in the waterfront neighborhood of Jeffries Point, East Boston. A 5-minute walk to lovely parks and the HarborWalk. And just ONE SUBWAY STOP to downtown Boston. We love Boston - and hope we can share it with you!

4.94 out of 5 average rating, 262 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, 267 reviews
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

Welcome to The Green Suite, a private condo within a historic home. The whole group will enjoy easy access to everything from this centrally located place. Just under a half a mile to all tourist attractions in Downtown Salem, but far enough away to be peaceful at night. Also a half mile from the commuter rail and a 40 minute ride from the airport. This listing includes one parking spot in an on site privately owned parking lot.

4.97 out of 5 average rating, 268 reviews
Guest favourite
Condo in Swampscott

Ocean View Coastal Retreat | Minutes from 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.

4.95 out of 5 average rating, 111 reviews
Top Guest favourite
Condo in Hampton Beach

Adorable beach cottage with kitchen

Make some memories at this unique and family-friendly beach front studio. Full kitchen and 3/4 bath, with WiFi and a smart TV. Limit 4 occupancy. One car parking directly in front of unit. The beach is directly across the street, so enjoy less than a minute walk to the quiet north end of Hampton beach. Short walking distance to all the store fronts and same block access to restaurants and yoga facility.

4.94 out of 5 average rating, 115 reviews
Superhost
A spacious living room features a gray sectional sofa adorned with decorative pillows in soft hues. A round coffee table with a textured surface is positioned in front of the sofa. Natural light filters through white window blinds, illuminating the light blue walls.
Condo in Lynn

High Rock Home-4BR, 2BA Modern, near downtown Lynn

High Rock Home, a "wicked awesome" modern downtown Lynn condo. Close proximity to restaurants & shops, beaches, outdoor activities, casino and transportation. You'll love the gourmet kitchen, high ceilings, deck and proximity to the water, Boston, Salem and many coastal towns. High Rock Home is perfect for couples traveling in groups, adventurers, business travelers, & families with children.

4.91 out of 5 average rating, 274 reviews
Guest favourite
A modern living space is presented with bright walls and stylish furnishings. A large dining table is positioned in the foreground, surrounded by dark chairs. The seating area features a light-colored sofa and an accent chair, complemented by artwork and a decorative wall-mounted antler.
Condo in Salem

Modern Farmhouse Condo Near Downtown Salem

Welcome to your modern farmhouse retreat! - Newly renovated condo in a quiet neighborhood - Elegant design with shiplap and bold decor - Private master with en-suite bathroom - Comfortable beds and central air - Smart TVs for entertainment - Close to Peabody Essex Museum and Salem Witch Museum (~15-20 minute walk) - No parties allowed

4.85 out of 5 average rating, 452 reviews

Popular amenities for Windham condo rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Weekly condo rentals

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

4.93 out of 5 average rating, 907 reviews
Top Guest favourite
The living area features a combination of deep blue walls and natural light from large windows. A light fixture hangs from the ceiling above a cozy seating arrangement, including a sectional sofa and a modern armchair. A decorative fireplace is accented by a mounted television.
Condo in Downtown Salem

Downtown beautiful renovation with parking

4.98 out of 5 average rating, 290 reviews
Guest favourite
A sandy pathway lined with beach grass leads toward the ocean, framed by wooden fencing. Vibrant hues of orange and pink paint the sky as the sun rises over the tranquil water, creating a serene coastal scene.
Condo in Salisbury

Oceanfront Penthouse at Salisbury Beaches

4.96 out of 5 average rating, 122 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!

4.96 out of 5 average rating, 114 reviews
Top Guest favourite
A small workspace features a marble-top table accompanied by a white chair with a fur throw. The green wall displays a variety of framed artwork and a small chalkboard with the word 'Welcome.' A mirror above the table reflects elements of the cozy room.
Condo in Downtown Salem

The Merchant's Carriage House - Downtown Salem

5.0 out of 5 average rating, 132 reviews
Top Guest favourite
An open living area showcases a warm ambiance with string lights overhead. A dining table is set for six, and a cozy seating arrangement includes a colorful armchair and a plush sofa. A wall-mounted TV is positioned beside vibrant artwork against the white walls.
Condo in Downtown Salem

*1710 Historic Downtown 2BR |Salem+Witch Trials

4.97 out of 5 average rating, 317 reviews
Top Guest favourite
An open living space features hardwood floors and a modern aesthetic. A sleek fireplace is mounted on the wall beneath a flat-screen TV. Bar stools with orange upholstery are positioned at the kitchen island, and a glass coffee table sits on a patterned area rug.
Condo in Gloucester

Boho Beach Condo for Ocean Escape

4.97 out of 5 average rating, 145 reviews
Top Guest favourite
The living area features a comfortable gray sofa adorned with blue accent pillows, flanked by two modern chairs. A glass coffee table sits atop a patterned rug, complemented by a small plant. Light enters through two windows with natural bamboo shades.
Condo in Portsmouth

Downtown City Gem Groups A+ Locale Privacy Parking

4.95 out of 5 average rating, 853 reviews

Pet-friendly condo rentals

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

4.98 out of 5 average rating, 123 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, 150 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, 173 reviews
Top Guest favourite
Condo in Winthrop

Truly Oceanfront! Spacious Family Petfriendly Home

4.99 out of 5 average rating, 242 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, 225 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, 268 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

4.96 out of 5 average rating, 136 reviews
Superhost
Condo in Somerville

Spacious, cozy home near Boston!

4.82 out of 5 average rating, 263 reviews

Condo rentals with a pool

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, 102 reviews
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, 112 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, 41 reviews
Top Guest favourite
Condo in Cambridge

“Luxury 2BR Cambridge | Pool + Parking”

4.93 out of 5 average rating, 27 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, 61 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 stone statue of a woman is depicted sitting gracefully, holding a wreath. An American flag flutters above, while a multi-story building is visible in the background, suggesting a seaside location.
Condo in Hampton Beach

Hampton 100 yards to beach

4.91 out of 5 average rating, 46 reviews

Destinations to explore