We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Windham Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
50 rentals in Windham.
Sort by:
Tripadvisor Sort

Modern cottage (Sleeps 6) on peaceful, small lake in Southern New Hampshire.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Quaint Cottage right on Long Pond in Dracut Massachsettes. Lake view,

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Lake Front Year Round Home On Angle Pond....

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Watch Eagles Soar at RiverBend: Waterfront, 4 Luxury suites, gourmet kitchen, Sm

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

TEWKSBURY, MA - RANCH HOUSE WITH GARAGE, 3 BEDS, 2 FULL BATHS - 14 DAY MAX STAY

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Private Water Front Home on Sunset Lake, Private Beach, Boating & Swimming

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Phillips Academy Area – Ideal for Families Visiting Campus & Touring New England

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Beautiful Lakefront 3b/ 2b updated home within an hour from Boston

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

FOR BUSINESS and PLEASURE TRAVELERS Studio

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

The Daffodil 1743 Getaway Apartment

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Windham rentals sent straight to your email!

Spacious & Gracious 3 Bedrooms, 2 Full Baths Ranch Living in central location!!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

at water's edge on quiet pond

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Why travel to Lake Winnipesaukee? Lakefront cottage in southern NH.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

NEW! Quiet Getaway - 19 Miles to Downtown Boston!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Gorgeous New Hampshire Lakefront Home 5 bed/3 Bath

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

A cosy house on Angle Pond in New England, USA

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

VILLA SOJOURN On The Merrimack entire home

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Charming 1920s Era Apt, Quiet Neighborhood 2 miles from Downtown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Quiet house mins away from the Airport and Hwy 93

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

The Mill House . This is a two story home with three bedrooms, 1.5 baths.

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Cozy, 2BR lake-side retreat and outdoor oasis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Richards Lakin House Apartment. 1 Bdrm apt for 3

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Stunning 4 Bedroom,2.5 Baths abuts Phillips Academy, walk to Town and Train

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

1 bedroom apartment: Clean, Spacious, Comfortable, Local to everything (Apt 1R)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

VILLA RIVIERA on the Merrimack River.

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Near Phillips Academy Andover. - Ask about long term rates.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Perfect for Traveling Professional

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Peaceful retreat for stays of 14 days and more. Panda room

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

For business and pleasure travelers. Blue room.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Holiday Deal! Beautiful 3 bed apartment within walking distance to everything!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Beautifully Furnished Private Retreat in Andover!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Gorgeous 1 Bed 1 Bath

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

FOR BUSINESS AND PLEASURE TRAVELERS Main Bedroom

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Private Room/Bath with Garden and Pond Views

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Tentrr Signature Site - Normanton Farms - Coleman Outfitted Site

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Full house on river. Enjoy kayaking, fishing & sunsets

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Spacious Apartment in Beautiful Southern New Hampshire

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Beach Vacation New England1828 Farmhouse away from crowds

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

For Business and Pleasure Travelers. Pink room.

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

★Couples/Business/Nomads★Quiet/Soothing/Relaxing★

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Beautiful 2bdrm condo with tons of character

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Tentrr Signature Site - Souhegan Serenade

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Townhouse in La Savina

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Tranquil setting in Private home

Holiday Rental House
1 bedroom
3 bathrooms
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

18th Century Farm House in Center of Carlisle

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

near Boston

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Midweek Special! Sunset Suite: close to beaches, parks, eateries & shops; privat

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Ames for Fun: Near town, parks, art studios; eateries, family friendly, sunset v

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Tentrr Signature Site - Souhegan Serenade

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

PRIVATE COUNTRY HOME

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
PreviousNext
1
Frequently Asked Questions about Windham