Family-friendly vacation rentals in Windham

4.99 out of 5 average rating, 290 reviews

A spacious home sits on a manicured lot, featuring a well-kept garden and an expansive driveway. The two-story structure boasts large windows and a welcoming entrance, with outdoor lighting enhancing its features during twilight. The attached garages are visible on the right.

Guest suite in Windham

Sunny, private and peaceful apartment!

Our home sit in a private and peaceful setting. It is perfect for the business travelers looking for a place to relax at the end of the day or anyone looking for a quiet place. Close to Castleton Banquet and Conference Center, Searles Castle, Canobie Lake Park, walking & biking trails, shopping and restaurant. Centrally located between Boston, beaches and mountain and lake region. Only 16 miles from Manchester Boston Regional Airport, 36 miles from downtown Boston, 3.5 miles from Interstate 93.

4.99 out of 5 average rating, 166 reviews

An inviting open-concept living area features a brown sectional sofa with a chaise, accented by throw pillows. A round coffee table sits in front, surrounded by a welcoming atmosphere of honeybee-themed decor, such as hexagon shelves on the wall. A workspace with a chair is positioned nearby.

Apartment in Billerica

Air Bee-n-Bee Hive-Unique Themed Stay, Coffee bar

Plan a unique and memorable stay at the Hive, a bee-themed apartment in a Boston suburb 21.1 miles from the city. Delight in the charming honeybee-inspired décor. Relax on the patio and enjoy the nearby chickens and geese – and especially their fresh eggs. You’ll love the entertainment options – 100s of free movies plus cable TV and access to streaming channels. Everything you need is here, from a full kitchen with a coffee bar to EV charger. Got work? A workspace and super-fast Wi-Fi await you.

4.97 out of 5 average rating, 143 reviews

The exterior of the home and attached apartment is shown, featuring a light-colored facade with dark trim. A paved driveway leads to a two-car garage, surrounded by landscaping of shrubs and trees. An American flag is displayed, providing a welcoming touch.

Apartment in Londonderry

The Birch Suite: Large, Cozy NH Themed Apartment

Our home and attached apartment is tucked away in a quiet neighborhood in southern NH, just minutes from major N/S highway Route 93. We are thrilled to offer our New Hampshire-themed apartment to individuals, couples and families. Each room is decorated to represent the most interesting aspects of our state: the purple lilac bathroom, the maple bedroom, the white birch living room and a large second bedroom/playroom we call "the state room" - a fun, educational room of all things New Hampshire.

4.93 out of 5 average rating, 304 reviews

An aerial view showcases a spacious property surrounded by lush trees, featuring a large private tennis court and half-basketball court. The well-manicured grounds are complemented by additional outdoor areas, highlighting a serene and inviting environment.

Home in Windham

One Level 2 bedroom suite on private cul-de-sac

Welcome to The Sama's Airbnb. Windham was recently named the #1 town in the Granite State. Here, you will enjoy a complete newly renovated private one level 2 bedroom suite complete with full kitchen, cozy living room, 40 inch LED TV with all channels, wifi, washer and dryer, new tennis court, 1/2 basketball court and pickleball, beautifully landscaped grounds on a private cul de sac yet close to Boston, beaches, mountains, shopping, great restaurants, Searles Castle, Canobie, & Tuscan Village.

4.93 out of 5 average rating, 119 reviews

A serene view of the calm lake is presented, framed by trees and surrounding greenery. The water reflects the clear sky, while homes are visible along the bank, creating a peaceful landscape perfect for relaxation.

Guesthouse in Salem

Large Private Guest House with Lake Views in NH

Just 36 miles north of Boston/Logan Airport.Enjoy lake views from this above garage private entrance guest house. Two private bedrooms (1 queen 1 full) with additional queen futon. Unit is clean & comfortable with 2 smart tv's, wifi, Keurig, microwave, minifridge/freezer. Explore the lake using 2 available kayaks. Two public beaches nearby. Parking for 3 cars. Minutes from Canobie Lake Park & Tuscan Village. 5 Wedding venues w/in 5 miles. Short drive to NH seacoast, white mountains &foliage.

4.95 out of 5 average rating, 231 reviews

A charming Victorian house is presented, featuring distinctive architectural elements such as a turret and steeply pitched roof. A flag is displayed at the entrance, while well-maintained shrubs and grass surround the property. The steps lead to a welcoming front door.

Apartment in Derry

Victorian Charm.

Welcome to your home away from home in this charming Victorian getaway! We offer character, convenience & close to 2000 sq ft living space. Enjoy your morning coffee in the turret, all the wonder of being outside (circular view), yet all comforts of the warmth within. We are 40 minutes from Boston, 1.5 hours south of the White Mountains, 1.9 miles from 93 N/S ramp. If mid-term rental is your goal, feel free to inquire. Free onsite parking. We look forward to hosting you in beautiful NH!

4.78 out of 5 average rating, 259 reviews

The exterior of a two-story building showcases a traditional design with white siding and dark blue shutters. A welcoming entrance is highlighted by a covered front porch and a set of stairs. Surrounding greenery adds to the inviting atmosphere.

Apartment in Amesbury

Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches

Unwind in the modern 1BR 1Bath apt in the heart of downtown Amesbury, just a stone's throw away from tasty local restaurants and attractions. This charming oasis is perfect for leisure guests looking to explore nearby beaches and towns while also being close to hospitals and colleges, catering to traveling nurses and professionals. ✔ Comfortable King Bedroom ✔ Cozy Living Room ✔ Fully Equipped Kitchen ✔ Smart TV ✔ Workspace ✔ Washer/Dryer ✔ High-Speed Wi-Fi ✔ Free Parking Learn more below!

4.88 out of 5 average rating, 336 reviews

A modern kitchen is presented with white cabinets and stainless steel appliances, including a refrigerator and oven. Granite countertops provide ample workspace, with a sink beneath a window. Natural light fills the area, enhancing the open and inviting atmosphere.

Apartment in Windham

The Cozy Corner Apartment

Cozy up during your next trip to the southern New Hampshire area! The Cozy Corner is a combination of style and comfort in so many ways from the double windows and sliding glass doors that flood the space with light to the airy and peaceful design that makes it feel like home. The Cozy Corner is a short drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston and NH Seacoast, close to Lakes Region, White mountains, and great skiing spots. 10 minutes from major shopping centers!

4.99 out of 5 average rating, 258 reviews

A spacious living area features a gray sofa and a patterned armchair, accompanied by a wooden coffee table. A small table holds a lamp and magazines. A doorway leads to the bedroom, while a kitchenette is visible in the background.

Guest suite in Merrimack

Guest suite with king bed and private entrance

Come and relax in our spacious one-bedroom basement guest suite that is comfortable and bright. It has a private entrance with off street parking. The suite has a large living area, bedroom with king bed and private bath . The location is an ideal 20 minutes from the Manchester/Boston Regional airport and 10 minutes from the Merrimack Premium Outlets as well as a wide variety of restaurants. Boston, skiing, the beach and the #1 most hiked mountain in the world are all about an hour away.

5 out of 5 average rating, 145 reviews

The studio features a spacious bed with white linens, accented by decorative throw pillows. A vibrant piece of art adorns the wall above the bed. A modern vanity area with a sink is visible, along with natural light filtering through windows that offer views of the surrounding woods.

Guest suite in Milford

New England Village Luxury Studio

Kick back and relax in this stylish studio! Our house is in a quiet neighborhood of older homes surrounded by woodlands yet conveniently located downtown, a half mile from our village green (Milford Oval). A short stroll over the river will take you to cafes, restaurants, pubs with live music, post office, library, shops & useful stores such as CVS. Whatever brings you…business, skiing, hiking, antiques, a family celebration or a romantic weekend away…we are looking forward to hosting you!

4.76 out of 5 average rating, 397 reviews

A cozy living area features a light-colored sofa adorned with plush throw pillows. Natural light floods in through large windows, illuminating the space. A tabletop and decorative plant are visible in the background, adding a touch of warmth to the inviting ambiance.

Apartment in Derry

Downtown Derry, Studio Apartment

Cozy up during your next trip to southern NH! Built in 1910, the home has been completely renovated. The Studio is a combination of elegance and comfort from the walls of windows that flood the space with light and scenic conservation/golf course views to the spacious backyard that is perfect for a peaceful escape. It is 5 minutes from i-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

4.82 out of 5 average rating, 515 reviews

A bright sunroom features large windows that provide scenic views of the surrounding greenery. A comfortable gray couch and a floral-patterned chair are arranged around a soft white area rug, creating a cozy space for relaxation.

Apartment in Derry

Downtown Derry, Loft Apartment

Cozy up during your next trip to southern NH! Built in 1910, the home has been completely renovated. The Loft is a combination of elegance and comfort from the walls of windows that flood the space with light and scenic conservation/golf course views to the spacious backyard that is perfect for a peaceful escape. It is 5 minutes from i-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Popular amenities for Windham family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 163 reviews

An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.

Home in Hopkinton

Hopkinton Mass 3+ Bedrooms - Great location!

4.93 out of 5 average rating, 176 reviews

A private outdoor area features a spacious hot tub surrounded by wooden walls and deck flooring. Soft lighting is provided by string lights overhead. A small table sits nearby for convenience, and a patterned rug adds a touch of comfort to the space.

Apartment in Woburn

Your Cozy 1 BR Apt & Relaxing Retreat

4.99 out of 5 average rating, 139 reviews

A modern coastal home featuring a light grey shingle exterior and a contrasting dark roof. The entrance showcases a well-defined porch with elegant lanterns and large windows, while a driveway leads to a two-car garage. Lush greenery surrounds the property, enhancing the seaside setting.

Home in Cape Neddick

Luxurious Oceanfront Property

4.87 out of 5 average rating, 114 reviews

Home in Merrimack

Pond-Front Passive Solar Architectural House

4.98 out of 5 average rating, 119 reviews

An outdoor tub is situated on a wooden deck, surrounded by vibrant autumn foliage. A red faucet provides a natural flow of water, while a small bowl of floating objects rests nearby. In the background, a glimpse of a serene lake can be seen through the trees.

Cabin in Stoddard

Boulder House - Extraordinary Luxury in the Woods!

4.95 out of 5 average rating, 209 reviews

A bright and airy living space showcases a combination of wooden beams and a warm color palette. A comfortable leather sofa faces a coffee table, with two green chairs positioned nearby. Large windows provide a view of the outdoors, while an inviting staircase leads to the upper level.

Home in Mont Vernon

Private Waterfront! Views, Hot Tub, King Bed

Farm stay in North Andover

The spacious room features a king-sized bed with soft bedding and decorative pillows. Natural wood accents support a pitched ceiling, while a chandelier provides ambient lighting. A cozy gas fireplace and a flat-screen TV are visible. Large windows allow natural light and views of the surroundings.

4.95 out of 5 average rating, 272 reviews

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

Cabin in Tilton Northfield

A charming country cabin is presented, featuring wooden shingle siding and red trim. A welcoming front door is set within a gabled frame. Surrounding greenery includes well-maintained bushes and trees, with a wooden privacy fence visible to one side.

4.95 out of 5 average rating, 257 reviews

Adorable Country Cabin with Hot Tub

Family- and pet-friendly home rentals

4.87 out of 5 average rating, 548 reviews

The exterior of The Word Barn is illuminated against a twilight sky, showcasing its distinct architectural features. Warm lights line the entrance, and large windows reveal a welcoming interior. Surrounding greenery adds to the tranquil ambiance of the private setting.

Barn in Exeter

The Word Barn, Exeter, NH

4.98 out of 5 average rating, 104 reviews

A traditional farmhouse is visible alongside a red barn, set against a backdrop of autumn foliage. The well-maintained lawn features neatly trimmed shrubs and trees, with the clear sky overhead highlighting the peaceful rural setting.

Home in Newton

Winnie's Place - Freshly Renovated 1800s Farmhouse

4.84 out of 5 average rating, 252 reviews

A cozy sleeping area features a spacious bed adorned with a patterned duvet and accent pillow. Light grey walls and large windows provide a bright atmosphere. Bedside tables with lamps flank the bed, and a textured area rug adds warmth to the hardwood flooring.

Apartment in Newburyport

Private Newburyport Studio w/bath

4.98 out of 5 average rating, 101 reviews

The exterior of Linden Cottage is showcased against a vibrant sunset, highlighting its classic New England style. The house features light yellow siding with blue shutters, a welcoming front door adorned with a wreath, and a neatly maintained lawn.

Home in Plaistow

Linden Cottage - comfort, connection, convenience

5 out of 5 average rating, 228 reviews

A bright yellow two-family home is positioned amidst greenery, featuring a welcoming entry with a red door. A small flowering tree adds a splash of color in front, while a large deck is visible in the background, perfect for outdoor gatherings.

Home in North Chelmsford

Newly renovated, spacious, clean, 3 bedroom home.

Apartment in Manchester-by-the-Sea

A spacious living area features a large, sectional sofa with neutral upholstery, oriented towards a wooden coffee table. Bright light filters through multiple windows, illuminating the room. A dining area with wooden chairs is visible in the background, along with built-in storage cabinets.

4.9 out of 5 average rating, 177 reviews

Modern Space With Pool Close To Singing Beach

4.94 out of 5 average rating, 120 reviews

An open-concept living area is highlighted by hardwood floors and a vaulted ceiling. A maintenance-free reef tank with ambient lighting is displayed on the wall. Modern seating options include a sectional sofa and chairs arranged around a coffee table, with large windows providing natural light.

Apartment in Westford

Large One Bedroom Apartment

4.79 out of 5 average rating, 169 reviews

A bright sleeping area is showcased with a queen-sized bed featuring crisp white bedding and decorative pillows in soothing greens. Three framed artworks hang above the bed, complementing the neutral wall color. A desk and chair are positioned nearby, with a stylish lamp on a side table.

Apartment in Manchester

Relaxing Retreat | Pet Friendly Apartment

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 106 reviews

A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.

Apartment in Brighton

Peaceful suite in Boston with city views

4.94 out of 5 average rating, 172 reviews

A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.

Home in North Andover

Nana-tucket Inn

4.86 out of 5 average rating, 205 reviews

The kitchen features modern cabinetry with a light grey finish and granite countertops. Stainless steel appliances include a refrigerator, dishwasher, oven, and microwave. A window allows natural light to illuminate the space, and oak flooring runs throughout, providing a warm atmosphere.

Condo in Wells

Two-Bedroom Condo on the Wells/Ogunquit town-line

4.97 out of 5 average rating, 105 reviews

Home in Weston

Spacious vacation unit in premium suburban town

4.84 out of 5 average rating, 194 reviews

A spacious studio apartment is presented, featuring a full bed with soft linens and decorative pillows. Natural light fills the room through large windows, which are dressed with elegant curtains. A modern seating area includes a sleek black sofa and an armchair, creating a comfortable relaxation space.

Apartment in Beachmont

Stylish and Cozy at Revere Beach

Guesthouse in West Roxbury

A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.

4.95 out of 5 average rating, 205 reviews

Country Cottage in the City

4.97 out of 5 average rating, 369 reviews

A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.

Apartment in Waltham

Cozy Private Studio Unit w/ Laundry and Parking!