Vacation rentals in Windham

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Top-rated vacation rentals in Windham

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Guest favorite

Apartment in Gorham

4.96 out of 5 average rating, 194 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

Enjoy the historical charm of one of Gorham's oldest homes. Come stay in a lovely private second floor, one bedroom apartment with private entry. Just walking distance from restaurants, the grocery store, laundromat, college campus and local trails. It offers private off-street parking for one car and it is located in the heart of Gorham village, a safe and family oriented community. Private bedroom with queen size bed and a full size futon provided. No backyard access. Full Kitchen. Full bath.

Jun 3 – 10

G$31,108 GYD per night

Guest favorite

Guest suite in Bridgton

4.98 out of 5 average rating, 165 reviews

Barn on Pleasant-walk to town

Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well maintained property provides a cozy living space. The loft features a kitchenette, a beautiful stone fireplace and a big, comfy reclining couch. Visit Bridgton this spring and summer, walking distance to Highland Lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

Jan 2 – 9

G$32,130 GYD per night

Guest favorite

Guest suite in New Gloucester

4.98 out of 5 average rating, 173 reviews

Peaceful Lakeside Suite w/Firepit and Kayaks

Open the double doors of your suite for direct access to a beautiful Maine lake. With a private entrance, the open concept apartment is in the walk-out basement of our log-cabin style home. Includes a kitchenette, private bathroom, enclosed unheated porch, large flat screen TV with DirecTV, washer & dryer. A patio with firepit is available (except when snow-covered). You may swim and use our kayaks and other boats, in season, at your own risk. Nice views. Quiet and peaceful. Enjoy star-gazing.

Jul 16 – 23

G$26,324 GYD per night

Guest favorite

Tiny home in Windham

4.98 out of 5 average rating, 132 reviews

Private riverside retreat

Private tiny house situated on the Pleasant river in Windham Maine surrounded by woods and nature! River is stocked with brook trout and lots of bass. Canoes are available for guest use to explore the river. The camp is located behind the main property ~500ft down a dirt road. 4X4 is recommended or you can park at the main house and it's a 3 minute walk. House is very comfortable with modern amenities. Running hot water, electricity, smart TV, wifi , firepit, outdoor shower, king sized bed.

Nov 15 – 22

G$33,509 GYD per night

Guest favorite

Guest suite in Portland

4.95 out of 5 average rating, 113 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

Oct 11 – 18

G$18,965 GYD per night

Guest favorite

Home in Gorham

4.99 out of 5 average rating, 138 reviews

Beautiful Home In Gorham Maine

Well appointed, bright and sunny apartment for two people in a quiet neighborhood. Large private back yard, formal gardens and pond, elevated deck, well stocked kitchen. 25 mins. to downtown Portland and the seacoast area. Minutes to local nature trails, swimming, kayaking, dining, supermarket & bakeries. ** NO PROFILE/REVIEWS? please provide a little info about whose coming, ie, name/age/occupation, reason of visit, etc, and any other info you wish to provide. Thank you!

Jul 26 – Aug 2

G$36,563 GYD per night

Guest favorite

Farm stay in Buxton

4.96 out of 5 average rating, 203 reviews

Little River Flower Farm - Cottage

Post & Beam Cottage, rustic knotty pine interior. Five miles to Gorham Center close to USM, 20 minutes to St. Josephs College on Sebago Lake, easy 30 minute drive to Portland, 12 miles to the PWM Jetport. Centrally located to many of Maine's finest breweries: Sebago Brewing, Mast Landing, Funky Bow, Nonsuch, Sea Dog, Barrel Souls, Bissell Brothers. Many local hiking trails including trails right here at our farm. Portland boasts of the finest restaurants in the state.

Mar 9 – 16

G$30,080 GYD per night

Guest favorite

Home in Cumberland

4.95 out of 5 average rating, 279 reviews

Rustic charm close to Portland

Peaceful and private. My home is a country getaway with unique charm and has a feeling like no other. Just voted the safest town to live in Maine, located close to downtown Portland, the Portland Jet Port, Freeport, beautiful Maine beaches, apple orchards, a Gorgeous wedding venue a mile away called Caswell Farm and close to trails for hiking, my home has many options. It's a great spot for a family to stay and the rental is the entire home.

Mar 2 – 9

G$39,005 GYD per night

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 219 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

May 29 – Jun 5

G$26,391 GYD per night

Guest favorite

Guest suite in Windham

4.92 out of 5 average rating, 151 reviews

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

Jun 13 – 20

G$24,010 GYD per night

Guest favorite

Cabin in Lovell

4.97 out of 5 average rating, 254 reviews

Secluded, cozy cabin nestled in the Maine woods

Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking.

Dec 22 – 29

G$23,709 GYD per night

Guest favorite

Guesthouse in Cumberland

4.97 out of 5 average rating, 153 reviews

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.

May 5 – 12

G$32,230 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Windham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Windham's top sights

Seacoast Adventure59 locals recommend

Walmart Supercenter14 locals recommend

Bob's Seafood43 locals recommend

Pat's Pizza23 locals recommend

Applebee's Grill + Bar4 locals recommend

Smitty's Cinema Windham25 locals recommend

Other great vacation rentals in Windham

Guest favorite

Guest suite in Scarborough

4.98 out of 5 average rating, 138 reviews

Beautiful, private apartment!! Great location!

Dec 9 – 16

G$25,214 GYD per night

Guest favorite

Cabin in Freeport

4.98 out of 5 average rating, 469 reviews

Cozy Cottage-Near Harbor & Park

May 14 – 21

G$32,637 GYD per night

Guest favorite

Cabin in Windham

5.0 out of 5 average rating, 14 reviews

Cozy Private Lake Getaway (Seasonal)

Oct 16 – 21

G$35,994 GYD per night

Guest favorite

Home in Windham

4.96 out of 5 average rating, 27 reviews

Private 3BR Ranch

Oct 22 – 29

G$38,574 GYD per night

Guest favorite

Guest suite in Standish

4.92 out of 5 average rating, 87 reviews

Steep Falls Escape, river & falls just steps away

Jun 7 – 14

G$24,077 GYD per night

Guest favorite

Guesthouse in Falmouth

4.96 out of 5 average rating, 24 reviews

The Herons Nest at The Mill

Jun 5 – 12

G$28,253 GYD per night

Guest favorite

Cottage in Windham

4.89 out of 5 average rating, 62 reviews

Covered Bridge Cottage - Maine woods and river

May 6 – 13

G$38,858 GYD per night

Guest favorite

Guest suite in Gorham

4.98 out of 5 average rating, 100 reviews

Farmhouse stay, near lakes and St. Joe's College

Sep 28 – Oct 5

G$36,293 GYD per night

Show all

Quick stats about vacation rentals in Windham

Total rentals
170 properties
Wifi availability
170 properties include access to wifi
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
130 properties are a good fit for families
Total number of reviews
6.2K reviews

Frequently Asked Questions

What are the most popular amenities for Cottage Rentals in Windham?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 30 homes with a kitchen, over 30 homes with free parking, over 30 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in apartment rentals in Windham?
Experience the best of Windham with our apartment rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Windham?
Yes! Work meets play with ease at over 80 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Windham?
Four-legged friends are welcome in Windham. Choose from more than 50 vacation rentals for guests traveling with pets.
Do house rentals in Windham have free parking?
Absolutely! We offer over 80 house rentals with free parking in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Windham have a kitchen?
Absolutely! We offer over 30 cottage rentals with a kitchen in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Windham have wifi?
Absolutely! We offer over 30 cottage rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have air conditioning?
Absolutely! We offer over 60 house rentals with air conditioning in Windham. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Windham

Top-rated vacation rentals in Windham

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Windham vacation rentals

Stay near Windham's top sights

Other great vacation rentals in Windham

Guest suite in Scarborough

Cabin in Freeport

Cabin in Windham

Home in Windham

Guest suite in Standish

Guesthouse in Falmouth

Cottage in Windham

Guest suite in Gorham

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

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

How much does it cost to stay in apartment rentals in Windham?

Are there vacation rentals with a dedicated workspace in Windham?

Are there pet-friendly vacation rentals in Windham?

Do house rentals in Windham have free parking?

Do cottage rentals in Windham have a kitchen?

Do cottage rentals in Windham have wifi?

Do house rentals in Windham have air conditioning?

Destinations to explore