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 29 – Dec 6

R2,592 ZAR per night

Guest favorite

Guest suite in Tyngsborough

4.98 out of 5 average rating, 215 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

R2,397 ZAR 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.

Feb 2 – 9

R2,836 ZAR 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

R2,486 ZAR per night

Superhost

Apartment in Windham

4.88 out of 5 average rating, 235 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.

Feb 8 – 15

R2,250 ZAR 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 24 – Jul 1

R4,689 ZAR 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).

Jul 22 – 29

R2,759 ZAR 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

R1,762 ZAR 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.

Dec 22 – 29

R4,584 ZAR 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.

Aug 25 – Sep 1

R2,168 ZAR 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!

Jan 4 – 11

R2,186 ZAR per night

Guest favorite

Guest suite in Milford

5.0 out of 5 average rating, 126 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

R2,067 ZAR 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

Sep 15 – 22

R2,436 ZAR per night

Guest favorite

Guesthouse in Derry

4.96 out of 5 average rating, 110 reviews

The Carriage House, A Modern Farmhouse

Nov 28 – Dec 5

R3,707 ZAR 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

R1,923 ZAR per night

Guest favorite

Apartment in Exeter

4.99 out of 5 average rating, 170 reviews

The Dragonfly

Dec 4 – 11

R2,015 ZAR per night

Superhost

Guest suite in Merrimack

4.85 out of 5 average rating, 131 reviews

Mini-Apartment in Quiet Neighborhood

Jun 27 – Jul 4

R1,763 ZAR per night

Guest favorite

Guesthouse in Wilton

4.95 out of 5 average rating, 572 reviews

Cottage beside a waterfall

Feb 14 – 21

R2,902 ZAR per night

Guest favorite

Guest suite in Littleton

4.91 out of 5 average rating, 313 reviews

Historic Loft with bathroom & kitchenette

Sep 14 – 21

R2,030 ZAR per night

Guest favorite

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

Aug 9 – 16

R2,287 ZAR per night

Show all

Other great vacation rentals in Windham

Guest favorite

Cottage in Windham

5.0 out of 5 average rating, 45 reviews

Quaint Cottage near Cobbetts Pond

Mar 22 – 29

R3,528 ZAR per night

Guest favorite

Home in Derry

4.87 out of 5 average rating, 60 reviews

Beautiful Garden Studio apartment

Oct 14 – 21

R1,508 ZAR per night

Superhost

Apartment in Salem

4.93 out of 5 average rating, 43 reviews

Chic Salem, NH Studio Apartment

Feb 10 – 17

R2,852 ZAR per night

Guest favorite

Guesthouse in Salem

4.9 out of 5 average rating, 29 reviews

Large Private Guest House with Lake Views

Sep 21 – 28

R2,925 ZAR per night

Guest favorite

Guesthouse in Westford

4.98 out of 5 average rating, 80 reviews

Detached Waterfront Guest House

Jun 3 – 10

R2,308 ZAR per night

Guest favorite

Vacation home in Derry

4.96 out of 5 average rating, 82 reviews

Little Lake House-Kayaking, Swimming & more

Mar 31 – Apr 7

R4,842 ZAR per night

Guest favorite

Cottage in Windham

5.0 out of 5 average rating, 18 reviews

Lakefront! Johnson Point Cottages-“Morningside”

Apr 5 – 12

R10,949 ZAR per night

Guest favorite

Apartment in Merrimack

5.0 out of 5 average rating, 6 reviews

Historic 2-Bedroom Apartment

Jul 12 – 19

R2,281 ZAR per night

Show all

Quick stats about vacation rentals in Windham

Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
2.7K reviews

Frequently Asked Questions

Where should I stay in Windham?
Make yourself at home in Windham by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in Windham Depot, and over 20 vacation rentals in West Windham.
Are there pet-friendly vacation rentals in Windham?
Four-legged friends are welcome in Windham. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Windham?
Yes! Work meets play with ease at over 20 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Windham?
Windham has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Windham have wireless internet?
Absolutely! We offer over 20 house rentals with wireless internet in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Windham. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Windham?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wireless internet, over 10 homes with a bbq area, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Windham vacation rentals

Top-rated vacation rentals in Windham

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Windham vacation rentals

Stay near Windham's top sights

Other great vacation rentals in Windham

Apartment in Andover

Guesthouse in Derry

Guest suite in Derry

Apartment in Exeter

Guest suite in Merrimack

Guesthouse in Wilton

Guest suite in Littleton

Guest suite in Peabody

Other great vacation rentals in Windham

Cottage in Windham

Home in Derry

Apartment in Salem

Guesthouse in Salem

Guesthouse in Westford

Vacation home in Derry

Cottage in Windham

Apartment in Merrimack

Quick stats about vacation rentals in Windham

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Windham?

Are there pet-friendly vacation rentals in Windham?

Are there vacation rentals with a dedicated workspace in Windham?

Are there family-friendly vacation rentals in Windham?

Do house rentals in Windham have wireless internet?

Do house rentals in Windham have a bbq area?

Do house rentals in Windham have air conditioning?

What are the most popular amenities for House Rentals in Windham?

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