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Gaylordsville Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Gaylordsville holiday rentals

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

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
8.6 out of 10, Excellent, (10)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$692
HK$951 total
includes taxes & fees
3 Jan - 4 Jan 2026
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior
New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury
Southbury
9.8 out of 10, Exceptional, (20)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is HK$665
HK$920 total
includes taxes & fees
29 Dec - 30 Dec
New One Bedroom Apartment Centrally Located in Southbury
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
Goshen
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is HK$688
HK$4,827 total
includes taxes & fees
4 Jan - 5 Jan 2026
CT Gate House Goshen CT, Gate House Goshen CT
Games room
Peaceful apartment on 3.5 acres w/ artist studio.

Peaceful apartment on 3.5 acres w/ artist studio.

Peaceful apartment on 3.5 acres w/ artist studio.
Brookfield
9.6 out of 10, Exceptional, (20)
"This was a nice get away for us that was not too far away from home."
United States
Isabella M.
Peaceful apartment on 3.5 acres w/ artist studio.
Microwave, oven, stovetop, dishwasher
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
2.0 star property
Southbury
10.0 out of 10, Exceptional, (1)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$884
HK$1,485 total
includes taxes & fees
29 Dec - 30 Dec
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
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.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
3.0 star property
Carmel
10.0 out of 10, Exceptional, (3)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,050
HK$2,166 total
includes taxes & fees
27 Dec - 28 Dec
Charming 1-bedroom apartment in Carmel with WiFi, AC
Exterior
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
1.0 star property
New Milford
8.0 out of 10, Very good, (1)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
The price is HK$1,166
HK$1,497 total
includes taxes & fees
27 Dec - 28 Dec
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
3 bedrooms, iron/ironing board, travel cot, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
2.0 star property
Holmes
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is HK$1,463
HK$4,206 total
includes taxes & fees
5 Jan - 6 Jan 2026
"Country outside the city " 3 bedrooms 2 full bathrooms
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

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
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is HK$1,295
HK$2,760 total
includes taxes & fees
5 Jan - 6 Jan 2026
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Outdoor dining
Hoppy Hill Farm House

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.6 out of 10, Exceptional, (4)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
The price is HK$778
HK$1,513 total
includes taxes & fees
11 Jan - 12 Jan 2026
Hoppy Hill Farm House
Fridge, microwave, oven, stovetop
Mid Century Modern Studio w/ Full Kitchen - Newly Built

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, (10)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is HK$1,516
HK$1,938 total
includes taxes & fees
29 Dec - 30 Dec
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Property grounds
The Hideaway

The Hideaway

The Hideaway
Brewster
10.0 out of 10, Exceptional, (6)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
United States
Rick C.
The price is HK$1,205
HK$2,461 total
includes taxes & fees
28 Dec - 29 Dec
The Hideaway
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is HK$1,183
HK$2,024 total
includes taxes & fees
27 Dec - 28 Dec
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Terrace/patio
Cozy cute Relaxing home

Cozy cute Relaxing home

Cozy cute Relaxing home
Southbury
8.8 out of 10, Excellent, (6)
"nice quiet area"
United States
Alex V.
The price is HK$1,400
HK$2,589 total
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy cute Relaxing home
Outdoor dining
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (34)
"Stunning property!!"
United States
Samantha
The price is HK$1,925
HK$3,457 total
includes taxes & fees
31 Dec - 1 Jan 2026
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Property grounds
Creekside Retreat Tent

Creekside Retreat Tent

Creekside Retreat Tent
New Milford
10.0 out of 10, Exceptional, (4)
"Absolutely beautiful location and wonderful hosts very romantic spot lots of hiking trails near and on premises me and my husband loved the fact we slept by the water and can hear the water running all night very peaceful and beautiful site ."
United States
yarelis t.
The price is HK$1,166
HK$1,497 total
includes taxes & fees
28 Dec - 29 Dec
Creekside Retreat Tent
Private kitchen
Tranquil 4-bedroom house in welcoming Poughquag neighborhood

Tranquil 4-bedroom house in welcoming Poughquag neighborhood

Tranquil 4-bedroom house in welcoming Poughquag neighborhood
2.0 star property
Poughquag
The price is HK$1,387
HK$2,431 total
includes taxes & fees
6 Jan - 7 Jan 2026
Tranquil 4-bedroom house in welcoming Poughquag neighborhood
Smart TV, fireplace, books
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (16)
"Great location and condition. Roome enough for everyone."
United States
Christopher H.
The price is HK$2,175
HK$4,764 total
includes taxes & fees
28 Dec - 29 Dec
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
Exterior
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
2.0 star property
Goshen
The price is HK$2,061
HK$4,125 total
includes taxes & fees
10 Jan - 11 Jan 2026
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
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.
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Top Gaylordsville Hotel Reviews

Ethan Allen Hotel

Ethan Allen Hotel

10/10 Excellent
"The staff was friendly, and the room was spacious. "
Lorena 1-night trip
Posted 3 days ago
Ethan Allen Hotel

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 holiday rental in Gaylordsville?

Yes, there are holiday rentals close to the most popular sights in Gaylordsville, or you can select a more secluded option if you're looking for a relaxing stay. Gaylordsville is known for its parks.

What are some of the best holiday rentals that Gaylordsville has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Gaylordsville offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Gaylordsville?

Choose from 4 Expedia holiday rentals in Gaylordsville for a memorable holiday.

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 wider area.

What’s a holiday rental in Gaylordsville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Gaylordsville. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip or a small group gathering.