Condo vacation rentals in Windham

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Top-rated condo rentals in Windham

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Top guest favorite
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
4.98 out of 5 average rating, 114 reviews

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).

Top guest favorite
A spacious living area is highlighted by framed windows that provide ample natural light and offer views of the sky. A modern couch and an antique roll-top desk are present, accompanied by a cozy armchair. A decorative star design in the area rug adds a unique touch.
Condo in Peabody
4.94 out of 5 average rating, 119 reviews

Peabody Penthouse Top of the World Sunset View

Enjoy sunrise/sunset panoramic view from the new 6th floor Penthouse Sanctuary, the highest point in Peabody! This thoughtfully decorated spacious Penthouse open floor plan is a place to retreat, recharge, write, envision, and to enjoy the best of life. A walk away from the NS Mall/Borders Books where the Logan Express arrives. Also a mile away are the running trails, lovely ponds and apple picking at the city run Brooksby farm and six miles away from historic Salem. You will love it here!

Top guest favorite
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
4.99 out of 5 average rating, 205 reviews

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!

Guest favorite
A comfortable living area features a large sectional sofa with an orange accent pillow. A wooden coffee table sits in front, complemented by a light-colored media console housing a mounted TV. Natural light enters through multiple windows, illuminating the gray walls.
Condo in Beverly
4.93 out of 5 average rating, 123 reviews

Downtown Beverly| Water view| 2 BR| Steps 2 beach

Welcome to beautiful Beverly, MA! —> Perfect North Shore getaway —> Views of Danvers River with outdoor deck and patio furniture —> Steps to Pleasant View Beach & Gillis Park —> Walking distance to restaurants, shops, beaches, and breweries —> Walking distance to new restaurant on the Beverly harbor —> 5 minute walk for train to Boston —> 1 mile to downtown Salem —> 2 Miles to Endicott, 3 miles to Landmark, 5.5 miles to Gordon College, 1 mile to Montserrat College —> Fully equipped kitchen

Guest favorite
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
4.87 out of 5 average rating, 118 reviews

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.

Top guest favorite
Condo in Hampton Beach
4.98 out of 5 average rating, 346 reviews

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.

Top guest favorite
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
4.96 out of 5 average rating, 113 reviews

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!

Top guest favorite
A living area displays a light-colored sofa adorned with patterned pillows, accompanied by two blue armchairs. A sleek work desk and a television are positioned near an elegant marble fireplace. Natural light fills the room, highlighting the wooden flooring and soft color palette.
Condo in Charlestown
4.98 out of 5 average rating, 154 reviews

Large 1+bed in historic Charlestown, Boston!

Large 1 BR condo. This is a brick 3 story home & the rental condo is on the 1st floor only. KING bed, work desk area, living room w/queen pull out bed, fully equipped kitchen & private deck/courtyard. Washer/dryer. Convenient walk to cafes & restaurants, Whole Foods, MBTA, Freedom Trail, Bunker Hill Monument, USS Constitution. Courtyard is broken down Dec-March & NO smoking in house and NO smoking in courtyard. Not suitable for children under 6 years old.

Top guest favorite
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
4.97 out of 5 average rating, 239 reviews

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.

Top guest favorite
Condo in Swampscott
4.94 out of 5 average rating, 102 reviews

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.

Top guest favorite
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
4.99 out of 5 average rating, 130 reviews

Modern Victorian close to Salem

Welcome to The Ulman! Enjoy a stylish experience in our centrally-located historic condo. We are walkable to exquisite beaches and parks as well as downtown Swampscott where you will find shops, restaurants & bars to explore. If you feel like hanging in, share a meal in our well stocked kitchen or a cocktail in the parlor. Perfect for a couples getaway, small family or a group of friends looking to explore the North Shore.

Guest favorite
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
4.9 out of 5 average rating, 134 reviews

Oceanview Condo

Amazing ocean view studio condo. Wake up to views of the Atlantic Ocean as you sip morning coffee on your private balcony. Prime location within walking distance of restaurants and all the action. Room is professionally cleaned and includes fresh bath towels, sheets, and pillows. The beach is directly across the street! The condo is 308 square ft and includes 1 queen and 1 full size futon in the sitting area.

Popular amenities for Windham condo rentals