South Windham Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Browse Select South Windham Vacation Homes

Thames River Retreat · CT College+Casinos+USCGA
Property grounds

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (9)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
The price is CA $527
CA $1,141 total
includes taxes & fees
Sep 1 - Sep 2
Thames River Retreat · CT College+Casinos+USCGA
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge
Property grounds

Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

8.0 out of 10, Very good, (9)
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge
Spacious Home Near Mohegan Sun
Fridge, microwave, stovetop, coffee/tea maker

Spacious Home Near Mohegan Sun

2.0 out of 10, (1)
"My stay at this rental was deeply unsettling and unsafe. The apartment itself has a creepy, neglected vibe, and it only got worst. A serious safety issue occured when a teenager in our group fell through a rotted, unstable deck/ a terrifying and completely preventable accident. Even more concerning, the entrance code to our apartment was the same code used for all other units in the building. This made me feel extremely unsafe as anyone from another unit could have accessed ours at any time....
The price is CA $399
CA $949 total
includes taxes & fees
Sep 8 - Sep 9
Spacious Home Near Mohegan Sun
Brand new home min. to casino- Inquire with the host about specific travel dates
Fridge, microwave, oven, stovetop

Brand new home min. to casino- Inquire with the host about specific travel dates

10.0 out of 10, Exceptional, (26)
"Great sleeping options and plenty of backup towels and bedding "
Brand new home min. to casino- Inquire with the host about specific travel dates
Victorian 4BR/2BA Modern Home
Dishwasher

Victorian 4BR/2BA Modern Home

9.6 out of 10, Exceptional, (15)
"Great place and stay was really clean and comfy"
Victorian 4BR/2BA Modern Home
Charming 2-bedroom house in marvelous Montville with WiFi, AC
Outdoor dining

Charming 2-bedroom house in marvelous Montville with WiFi, AC

8.8 out of 10, Excellent, (3)
"Perfect for what we needed for an overnight stay."
Charming 2-bedroom house in marvelous Montville with WiFi, AC
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
Fridge, microwave, oven, stovetop

Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT

10.0 out of 10, Exceptional, (1)
"Spacious, clean and comfortable home. Nice neighborhood near a nice park and trails . Beds were comfortable, kitchen had the pots and pans we needed for dinner and breakfast. Perfect space for us and our 3 adult boys. "
The price is CA $218
CA $455 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
Fridge, microwave, oven, stovetop

4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

10.0 out of 10, Exceptional, (3)
"It was a pleasure staying here . The owner was always available. The house was updated and felt like home "
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
Magnificent 5BR/2BA Near Casinos
Microwave, oven, dishwasher, toaster

Magnificent 5BR/2BA Near Casinos

9.4 out of 10, Exceptional, (3)
"While we found the property to be mostly as advertised, we gave it a 4 star rating for two reasons: the pictures make the rooms seem larger than reality and the yard/outside space was unkempt. The potential to have a 5 star experience is there with just a little bit more attention and care. We would recommend the stay but just know these limitations."
Magnificent 5BR/2BA Near Casinos
You and your Family deserve a break. Relax and enjoy lake front living
Outdoor dining

You and your Family deserve a break. Relax and enjoy lake front living

10.0 out of 10, Exceptional, (50)
"Every thing was great, nice property. Highly recommend."
You and your Family deserve a break. Relax and enjoy lake front living
Spacious, unique barn with beautiful views.
Interior

Spacious, unique barn with beautiful views.

10.0 out of 10, Exceptional, (1)
"This is a very unique and comfy place. Kids regretted that they only got to spend two nights here. I would mind spending more time hanging out in this place either myself! "
The price is CA $229
CA $363 total
includes taxes & fees
Sep 3 - Sep 4
Spacious, unique barn with beautiful views.
Amazing lake house with everything you need!
Dining

Amazing lake house with everything you need!

9.8 out of 10, Exceptional, (16)
"Look ing forward to booking again. Summer would be great to use the lake.Brad was very nice and easy to get ahold of. Loved this place!!!!"
Amazing lake house with everything you need!
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Outdoor dining

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

9.4 out of 10, Exceptional, (15)
"Highly recommend for a peaceful location that offers everything you need to feel at home. "
The price is CA $186
CA $411 total
includes taxes & fees
Sep 7 - Sep 8
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Cozy 2 Bedroom Family Stay
Private kitchen

Cozy 2 Bedroom Family Stay

9.2 out of 10, Wonderful, (12)
"We had a great stay in Manchester! Quick walk to stores, restaurants, and Main St Manchester. The apartment was clean and spacious. Would definitely recommend & stay here again!"
Cozy 2 Bedroom Family Stay
The Lake House
Terrace/patio

The Lake House

9.8 out of 10, Exceptional, (17)
"We enjoyed our stay! The house was clean and comfortable, with a beautiful view!"
The Lake House
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest
Dining

Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest

10.0 out of 10, Exceptional, (56)
"This was a great and spacious property for our recent trip to the area for a family wedding. Everything was clean and as described with very responsive hosts!"
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest
Hidden Gem Quiet Dead-End St Near All Casino
Fridge, microwave, oven, stovetop

Hidden Gem Quiet Dead-End St Near All Casino

8.6 out of 10, Excellent, (8)
"Our family enjoyed our stay very much! Very comfortable beds. Great communication. We would stay again. "
Hidden Gem Quiet Dead-End St Near All Casino
Historical Blvd. Cheney Bros HillTop Mansion
Fridge, microwave, oven, stovetop

Historical Blvd. Cheney Bros HillTop Mansion

9.2 out of 10, Wonderful, (14)
"I found this location over a year ago for my son’s college graduation weekend. It worked out perfectly to have some open space to hang out and play games in between all of the festivities. "
Historical Blvd. Cheney Bros HillTop Mansion
Stunning Lakeside Retreat
Exterior

Stunning Lakeside Retreat

9.0 out of 10, Wonderful, (6)
"Great stay. Had everything we needed. Peaceful "
Stunning Lakeside Retreat
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Property grounds

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

10.0 out of 10, Exceptional, (66)
"1st time to the upper East coast. We chose this house because it's so close to so many amazing cities. We loved the location and the day trips to New York, Connecticut, Rhode Island, and Massachusetts. "
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Windham Hotel Reviews

Find out more about South Windham

Find out more about South Windham

South Windham Vacation Homes information

Number of reviews
Accommodation
116 Vacation Homes
Lowest Price
CA $191
Highest Price
CA $527

Explore a world of travel with Expedia

Explore a world of travel with Expedia