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Gaylordsville Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Gaylordsville vacation rentals

Property grounds

Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (8 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
The price is ￥13,008
￥21,698 total
includes taxes & fees
Jul 21 - Jul 22
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
The price is ￥17,864
￥33,620 total
includes taxes & fees
Jul 28 - Jul 29
Hoppy Hill Farm House
Smart TV, fireplace, books

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, (19 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥31,668
￥40,803 total
includes taxes & fees
Jul 27 - Jul 28
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Interior

Architect-Designed Dome on Private 7-Acre Retreat

Architect-Designed Dome on Private 7-Acre Retreat
Dover Plains
The price is ￥40,194
￥80,008 total
includes taxes & fees
Jul 21 - Jul 22
Architect-Designed Dome on Private 7-Acre Retreat
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (34 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
The price is ￥15,347
￥20,898 total
includes taxes & fees
Aug 10 - Aug 11
Cozy One Bedroom Apartment Centrally Located in Southbury
TV, fireplace, books

The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (2 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 ￥72,573
￥119,024 total
includes taxes & fees
Aug 14 - Aug 15
The Little Lake Cabin with hot tub
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.
Watertown
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is ￥17,864
￥23,792 total
includes taxes & fees
Jul 21 - Jul 22
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Outdoor dining

Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (55 reviews)
"Amazing weekend stay! The place was clean, cozy, and thoughtfully prepared. The host was responsive and welcoming. Would definitely book again!"
United States
Kelsey
The price is ￥203,874
￥334,738 total
includes taxes & fees
Aug 18 - Aug 19
Candlewood Lake Retreat with Private Dock
Outdoor dining

Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (4 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
The price is ￥13,008
￥21,698 total
includes taxes & fees
Jul 21 - Jul 22
Glamping, family fun, pet friendly
Internet, bed sheets

Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
The price is ￥16,240
￥29,921 total
includes taxes & fees
Jul 21 - Jul 22
Welcome to Sweet Abby Rose!
Property grounds

Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots

Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Danbury
10.0 out of 10, Exceptional, (1 review)
The price is ￥54,079
￥90,936 total
includes taxes & fees
Jul 21 - Jul 22
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Cookware/dishes/utensils

Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.6 out of 10, Exceptional, (10 reviews)
"Great spot "
United States
Mike P.
The price is ￥73,080
￥125,535 total
includes taxes & fees
Jul 27 - Jul 28
Awesome Lake Home with tons of fun!
Interior

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is ￥39,463
￥52,976 total
includes taxes & fees
Jul 21 - Jul 22
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
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.
Carmel Hamlet
9.8 out of 10, Exceptional, (17 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥32,886
￥63,976 total
includes taxes & fees
Jul 22 - Jul 23
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Outdoor dining

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, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is ￥23,678
￥37,501 total
includes taxes & fees
Jul 26 - Jul 27
The Perch in the Purchase -- Cozy, unique, and private
Interior

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, (6 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 ￥64,960
￥136,502 total
includes taxes & fees
Jul 26 - Jul 27
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Interior

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, (11 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is ￥34,916
￥44,701 total
includes taxes & fees
Jul 21 - Jul 22
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Exterior

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
9.6 out of 10, Exceptional, (4 reviews)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
The price is ￥51,968
￥79,732 total
includes taxes & fees
Jul 21 - Jul 22
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Coffee/tea maker, fridge, microwave, oven

"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 ￥39,171
￥101,448 total
includes taxes & fees
Aug 19 - Aug 20
"Country outside the city " 3 bedrooms 2 full bathrooms
Coffee/tea maker, fridge, microwave, oven

The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is ￥47,356
￥61,322 total
includes taxes & fees
Jul 23 - Jul 24
The Jefferson Guest House, Spacious, Special Views
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

8/10 Good
"A nice hotel with lots of local restaurants and things to do. I have stayed many times when visiting the area and will again"
Stephanie 2-night trip
Posted 12 hours 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:

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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?

Lakefront Summer Stunner in New England Just 2 Hours From NYC: This vacation home rental near Gaylordsville is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a private yard and a selection of games.

How many vacation rentals are there in Gaylordsville?

Choose from 4 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 Lake Waramaug State Park 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.