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Gaylordsville Vacation Rentals

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Our top choices for Gaylordsville vacation rentals

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
Jun 29 - Jun 30
Total with taxes and fees
Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
$180 nightly
The price is $204
Jun 23 - Jun 24
Total with taxes and fees
Hoppy Hill Farm House

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
$175 nightly
The price is $198
Jun 23 - Jun 24
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

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 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
$251 nightly
The price is $272
Jun 23 - Jun 24
Total with taxes and fees
Charming 1-bedroom apartment in Carmel with WiFi, AC

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.
$119 nightly
The price is $134
Jul 7 - Jul 8
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

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, (14 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
$410 nightly
The price is $444
Jun 29 - Jun 30
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
$260 nightly
The price is $281
Jun 24 - Jun 25
Total with taxes and fees
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

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, (15 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
$187 nightly
The price is $212
Jun 23 - Jun 24
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built

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
$203 nightly
The price is $230
Jun 23 - Jun 24
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private

"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.
$530 nightly
The price is $600
Jun 23 - Jun 24
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
$254 nightly
The price is $275
Jun 28 - Jun 29
Total with taxes and fees
The Tipsy Gypsy - Studio Apartment

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.
$374 nightly
The price is $374
Jun 24 - Jun 25
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views

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)
"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.
$433 nightly
The price is $490
Jun 23 - Jun 24
Total with taxes and fees
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

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
$118 nightly
The price is $134
Jun 29 - Jun 30
Total with taxes and fees
Glamping, family fun, pet friendly

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, (3 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.
$718 nightly
The price is $812
Jun 23 - Jun 24
Total with taxes and fees
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (9 reviews)
"Great spot "
United States
Mike P.
$633 nightly
The price is $716
Jun 28 - Jun 29
Total with taxes and fees
Awesome Lake Home with tons of fun!

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, (20 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.
$902 nightly
The price is $978
Jun 24 - Jun 25
Total with taxes and fees
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Whispering Estate Guest House - Countryside Getaway

Whispering Estate Guest House - Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
$778 nightly
The price is $882
Jun 23 - Jun 24
Total with taxes and fees
Whispering Estate Guest House - Countryside Getaway

Serene 2-bedroom spacious apartment

Serene 2-bedroom spacious apartment
Carmel Hamlet
$310 nightly
The price is $336
Jul 4 - Jul 5
Total with taxes and fees
Serene 2-bedroom spacious apartment
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

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 $444 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?

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 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 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.