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Gaylordsville Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Gaylordsville vacation rentals

Exterior

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

2. 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.
$181 nightly
The price is $205
Aug 10 - Aug 11
Total with taxes and fees
Hoppy Hill Farm House
Smart TV, fireplace, books

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

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (22 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
$186 nightly
The price is $211
Aug 9 - Aug 10
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Interior

4. Architect-Designed Dome on Private 7-Acre Retreat

Architect-Designed Dome on Private 7-Acre Retreat
Dover Plains
$431 nightly
The price is $487
Aug 10 - Aug 11
Total with taxes and fees
Architect-Designed Dome on Private 7-Acre Retreat
TV, fireplace, books

5. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (3 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.
$643 nightly
The price is $728
Aug 14 - Aug 15
Total with taxes and fees
The Little Lake Cabin with hot tub
Cookware/dishes/utensils

6. Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (11 reviews)
"Nicole is a wonderful host. We had a fantastic stay at her house. The home was beautifully prepared, and we felt very comfortable throughout our visit. Even though it was a rainy weekend, we were still able to enjoy the huge hot tub and had a great time playing the card games and board games provided. Thank you!!"
United States
W Y.
$677 nightly
The price is $767
Aug 16 - Aug 17
Total with taxes and fees
Awesome Lake Home with tons of fun!
Outdoor dining

7. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (56 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
$1,992 nightly
The price is $2,254
Aug 25 - Aug 26
Total with taxes and fees
Candlewood Lake Retreat with Private Dock
Property grounds

8. 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.
$118 nightly
The price is $134
Aug 10 - Aug 11
Total with taxes and fees
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Property grounds

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.
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Property grounds

10. 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)
$492 nightly
The price is $557
Aug 24 - Aug 25
Total with taxes and fees
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
1 bedroom, internet, bed sheets

11. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
$170 nightly
The price is $184
Aug 9 - Aug 10
Total with taxes and fees
Welcome to Sweet Abby Rose!
Interior

12. 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.
$743 nightly
The price is $841
Aug 23 - Aug 24
Total with taxes and fees
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Exterior

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
9.6 out of 10, Exceptional, (4 reviews)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
$434 nightly
The price is $491
Aug 9 - Aug 10
Total with taxes and fees
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Coffee/tea maker, fridge, microwave, oven

14. "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.
$525 nightly
The price is $594
Sep 7 - Sep 8
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
TV, fireplace

15. 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, (18 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
$389 nightly
The price is $422
Aug 9 - Aug 10
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Interior

16. 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
$240 nightly
The price is $272
Aug 16 - Aug 17
Total with taxes and fees
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Coffee/tea maker, fridge, microwave, oven

17. 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.
$393 nightly
The price is $393
Aug 18 - Aug 19
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
Property grounds

18. 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
9.4 out of 10, Exceptional, (10 reviews)
"Such a lovely cabin - so many details to make for an incredible stay. Amazing location - lake, mountains! Wylda was wonderful."
United States
Clare
$319 nightly
The price is $346
Aug 13 - Aug 14
Total with taxes and fees
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Outdoor dining

19. 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
$204 nightly
The price is $231
Aug 9 - Aug 10
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
Smart TV, fireplace, video games, DVD player

20. Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Place was beautifully done, it’s obvious they take care of their place. The hosts were thoughtful and attentive, will definitely visit again. "
United States
Jasmine G.
$900 nightly
The price is $975
Aug 10 - Aug 11
Total with taxes and fees
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
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

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"I always love to stay at the Litchfield Inn. They have added a swimming pool out back which is absolutely fantastic, with a lovely pool house with a terrific shower. Breakfast is always terrific, and the rooms are always comfortable."
Nisse 1-night trip
Posted 2 hours ago
The Litchfield Inn

Find out more about Gaylordsville

Everything you need to know about Gaylordsville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gaylordsville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gaylordsville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gaylordsville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gaylordsville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Gaylordsville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $134 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gaylordsville rentals

At Expedia, we put the best Gaylordsville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Gaylordsville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gaylordsville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gaylordsville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 Fall Foliage in New England Just 2 Hours From NYC: This vacation home 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.