Windham vacation rentals

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Top-rated vacation rentals in Windham

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

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Guest favorite

Guest suite in Windham

4.99 out of 5 average rating, 243 reviews

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.

Nov 30 – Dec 7

G$28,165 GYD per night

Guest favorite

Guest suite in Tyngsborough

4.98 out of 5 average rating, 216 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Guests can enjoy our home's private suite on a lovely small lake with a panoramic view, a spa-like bathroom, cotton linens, and a comfy bed. A/C and a fireplaced living room. Quietly watch lake nature or boats going by, or venture out to swim, kayak, or fish. Enjoy Lowell's mill history and it's national park, take a forest walk nearby, or drive 10 min. to Nashua, NH for its many restaurants and tax-free shopping. 1 hr from Boston and central to New England highlights. Low cleaning fees!

Aug 12 – 19

G$26,046 GYD per night

Guest favorite

Home in Windham

4.92 out of 5 average rating, 259 reviews

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.

Dec 26 – Jan 2

G$31,137 GYD per night

Guest favorite

Apartment in Londonderry

4.97 out of 5 average rating, 101 reviews

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.

Mar 1 – 8

G$27,004 GYD per night

Superhost

Apartment in Windham

4.88 out of 5 average rating, 236 reviews

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.

Jan 22 – 29

G$24,172 GYD per night

Guest favorite

Apartment in Windham

4.87 out of 5 average rating, 179 reviews

The Estate Escape with Hottub

The apartment is new with high-end finishes, but there is still a storage container outside in the front of the house. (See pictures.) Cozy up during your next trip to southern New Hampshire! The Estate Escape is a perfect place for a peaceful escape with its own hot tub. The Estate Escape is minutes away from Canobie Lake Park, Castleton, and La Belle Winery. It is a short drive to Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Jun 10 – 17

G$38,984 GYD per night

Guest favorite

Loft in Derry

4.99 out of 5 average rating, 540 reviews

Comfort and Convenience in a Private Studio

*Please note that we are located on a main road * Welcome! No matter what brings you to Derry, we guarantee your comfort and convenience. Our 400 square foot studio boasts privacy, style, and value. The apartment is simple, modern, and warm. Coffee, tea, and treats are provided; we want you to feel like you are home away from home. Curl up for your favorite show with Hulu Live and enjoy your morning coffee out on the balcony. The space accommodates 2 comfortably (with room for up to 4).

Jun 12 – 19

G$23,566 GYD per night

Guest favorite

Guest suite in Merrimack

4.99 out of 5 average rating, 149 reviews

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.

Jun 10 – 17

G$19,139 GYD per night

Guest favorite

Cottage in Windham

4.9 out of 5 average rating, 140 reviews

Little House on the Pond

PLEASE READ "OTHER THINGS TO NOTE" BEFORE BOOKING. Our "Happy Place" feels far, but is close to everything! Tucked in the woods in a small lake community, our tiny cottage is bright and cozy. Our fully appointed cottage has everything you need to be comfortable; heat, A/C, cotton linens, fluffy towels, BBQ, fire pit... even an outside shower. There's a hammock for naps, kayaks for paddling, beach chairs in the shed and a short walk leads to your spot in the sand and cool water.

Jul 24 – 31

G$49,802 GYD per night

Guest favorite

Guest suite in Hollis

4.98 out of 5 average rating, 113 reviews

Pine Estate - Private suite

Welcome to our spacious guesthouse located - 2 miles from Nashua - 5 minutes drive to the highway - 40 minutes to Boston and minutes from Hollis. Hollis is an active farming community offering beautiful orchards, nature paths, art studios and a winery. Beautiful private yard with a large patio where you can relax and enjoy nature at its best. Our place is ideal for a weekend get-away or business travelers. Please note there will be no exception to the no pets policy.

Jun 27 – Jul 4

G$23,880 GYD per night

Guest favorite

Apartment in Derry

4.95 out of 5 average rating, 193 reviews

Victorian Charm.

Welcome travelers to your home away from home, in this stylish 1000sqft Victorian getaway! We offer charm, character & convenience. Enjoy your morning coffee in the turret, all the wonder of being outside (5 window view), yet all comforts of the warmth within. We are 40 minutes from Boston & 1.5 hours south of the White Mountains. We are 1.9 miles from 93N/S ramp. Free Private, onsite parking & Private entrance. We look forward to hosting you in beautiful NH!

Dec 23 – 30

G$24,618 GYD per night

Guest favorite

Guest suite in Milford

5.0 out of 5 average rating, 127 reviews

Spacious Souhegan Getaway

We would be happy to welcome you to our spacious walk-out basement apartment that features a comfortable and stylish living space. The apartment decor is warm and contemporary, with a large living and eating area, modest kitchenette, bedroom with queen size bed, and fully appointed bathroom. We are close to downtown Milford and 30 minutes from Nashua and Manchester, as well as an easy drive to Merrimack Premium Outlets.

Jul 14 – 21

G$22,456 GYD per night

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

Walmart Supercenter4 locals recommend

The Common Man11 locals recommend

Searles Castle4 locals recommend

Old School Bar & Grill6 locals recommend

Griffin Park4 locals recommend

Mary Ann's Diner5 locals recommend

Other great vacation rentals in Windham

Guest favorite

Apartment in Andover

4.92 out of 5 average rating, 114 reviews

Villa Ricci

Dec 27 – Jan 3

G$26,398 GYD per night

Guest favorite

Apartment in Exeter

4.99 out of 5 average rating, 170 reviews

The Dragonfly

Mar 12 – 19

G$21,895 GYD per night

Guest favorite

Guest suite in Derry

4.92 out of 5 average rating, 142 reviews

Derry home with year round amenites

Sep 28 – Oct 5

G$20,896 GYD per night

Superhost