Lodging Image

Gaylordsville Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Gaylordsville vacation rentals

A rustic cabin surrounded by a forest with a stream in the foreground.

1. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is ￥56,519
￥97,563 total
includes taxes & fees
Oct 28 - Oct 29
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A living room with a fireplace, two armchairs, a sofa, and a TV.

2. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is ￥30,865
￥39,452 total
includes taxes & fees
Oct 29 - Oct 30
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

3. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is ￥10,684
￥22,734 total
includes taxes & fees
Nov 3 - Nov 4
Cozy private room in a shared home with a Full-size bed and private bathroom.
A bedroom with a bed, a dresser, and a window with curtains.

4. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
The price is ￥83,097
￥137,901 total
includes taxes & fees
Oct 26 - Oct 27
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

5. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (6 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The price is ￥50,259
￥90,483 total
includes taxes & fees
Oct 26 - Oct 27
The Little Lake Cabin with hot tub
A living room with a fireplace, bookshelves, a television, and a comfortable seating area.

6. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
Sharon Retreat w/ Private Yard
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

7. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (6 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is ￥35,613
￥73,007 total
includes taxes & fees
Nov 15 - Nov 16
Escape to Bantam Lake- With Fireplace and Hot tub!
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

8. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (20 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is ￥34,030
￥43,725 total
includes taxes & fees
Oct 26 - Oct 27
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

9. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is ￥60,275
￥102,357 total
includes taxes & fees
Nov 11 - Nov 12
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

10. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is ￥31,482
￥91,301 total
includes taxes & fees
Nov 2 - Nov 3
"Country outside the city " 3 bedrooms 2 full bathrooms
A hot tub in a backyard with a house, trees, and a clear sky.

11. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is ￥427,356
￥554,769 total
includes taxes & fees
Oct 22 - Oct 23
Las Flores Villa
A multi-story house with a dock and boats, surrounded by dense forest.

12. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
The price is ￥57,231
￥199,705 total
includes taxes & fees
Oct 26 - Oct 27
North Cliff House - Private Dock & Sauna
A white house with a steeply pitched roof and a small tower-like structure.

13. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.8 out of 10, Exceptional, (8 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
The price is ￥50,650
￥78,248 total
includes taxes & fees
Oct 25 - Oct 26
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A white house with a wooden staircase leading to a porch.

14. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (38 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is ￥16,382
￥22,006 total
includes taxes & fees
Nov 2 - Nov 3
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

15. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is ￥23,932
￥37,691 total
includes taxes & fees
Oct 28 - Oct 29
The Perch in the Purchase -- Cozy, unique, and private
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

16. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (7 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is ￥63,312
￥131,607 total
includes taxes & fees
Oct 26 - Oct 27
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A house surrounded by a dense forest with a hammock and a small shed.

17. Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
9.6 out of 10, Exceptional, (4 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

18. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is ￥16,619
￥22,278 total
includes taxes & fees
Nov 16 - Nov 17
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A wooden deck with a lounge chair and a table, a small wooden house with a door and windows, and a wooden fence.

19. Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Carmel
9.0 out of 10, Wonderful, (13 reviews)
"Perfect little getaway, adorable space and wonderfully accommodating hosts."
United States
Susan
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

20. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥35,138
￥66,213 total
includes taxes & fees
Nov 9 - Nov 10
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gaylordsville Hotel Reviews

Wyndham Southbury

Wyndham Southbury

8/10 Good
"Desk staff very accommodating. Restaurant at bar had very good food options. Room needed some updated renovating, I think the hotel may be in process of renovation of rooms. Overall had a very pleasant experience."
Catherine 4-night trip
Posted 2 hours ago
Wyndham Southbury

Find out more about Gaylordsville

Search for holiday rentals in Gaylordsville on Expedia! You can easily find your home rentals, villas, holiday apartments in Gaylordsville using one of the methods below:

  • View our selection of featured holiday rentals in Gaylordsville
  • Use the map to find apartments and other holiday homes in the Gaylordsville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Gaylordsville while they last

Look no further and take a look at our great range of rental properties in Gaylordsville!

Frequently asked questions

Can I find a vacation rental in Gaylordsville?

Yes, we have vacation rentals near popular sights in Gaylordsville, or you can select a secluded option if you're looking for a relaxing stay. Gaylordsville is known for its parks.

What are some of the best vacation home rentals in Gaylordsville?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental near Gaylordsville offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Gaylordsville?

Choose from 3 Expedia vacation rentals in Gaylordsville for a memorable vacation.

What’s there to see and do in Gaylordsville?

Housatonic River and Emmanuel Williamson Park are a couple of lovely local spots to get outside and enjoy nature. Mildred Strauss and James Morrissey Family Nature Preserves and Bull's Bridge are a couple of places you'll find in the larger area.

What’s a vacation rental in Gaylordsville like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Gaylordsville. Vacation rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for small groups.