A forest with tall trees and a winding path.

Gaylordsville Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Gaylordsville vacation rentals

A covered outdoor area with a wooden deck and a view of a grassy landscape with trees and a distant white building.

1. 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.
$182 nightly
The price is $206
Sep 7 - Sep 8
Total with taxes and fees
Hoppy Hill Farm House
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

2. 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
$128 nightly
The price is $144
Sep 1 - Sep 2
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
A living room with a fireplace, two armchairs, a sofa, and a TV.

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, (23 reviews)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
$189 nightly
The price is $214
Sep 1 - Sep 2
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A covered outdoor kitchen with a grill, bar stools, and a refrigerator stocked with snacks.

4. Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (5 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
$118 nightly
The price is $134
Sep 1 - Sep 2
Total with taxes and fees
Glamping, family fun, pet friendly
A white house with a wooden staircase leading to a porch.

5. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (36 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
$108 nightly
The price is $121
Sep 7 - Sep 8
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

6. 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.
$109 nightly
The price is $122
Sep 1 - Sep 2
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

7. 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.
$171 nightly
The price is $185
Sep 1 - Sep 2
Total with taxes and fees
Welcome to Sweet Abby Rose!
A white house with a grey roof, a balcony with a blue umbrella, and a visible chimney.

8. 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
$207 nightly
The price is $234
Sep 2 - Sep 3
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
Two camping tents set up in a forest with chairs and a wooden platform nearby.

9. 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, (11 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.
$142 nightly
The price is $160
Sep 7 - Sep 8
Total with taxes and fees
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Two tents set up in a forest with a table and chairs in front.

10. Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly

Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly
Dover Plains
10.0 out of 10, Exceptional, (5 reviews)
"Fun place with a variety of activities including hot tub, miniature golf, corn bag toss, etc. "
United States
Tania
$127 nightly
The price is $144
Sep 7 - Sep 8
Total with taxes and fees
Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

11. 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, (15 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
$245 nightly
The price is $277
Sep 1 - Sep 2
Total with taxes and fees
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

12. "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.
$518 nightly
The price is $585
Sep 15 - Sep 16
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

13. 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, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
$393 nightly
The price is $426
Sep 8 - Sep 9
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

14. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
$250 nightly
The price is $283
Sep 1 - Sep 2
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A room with a bed, a couch, a desk with a computer, and various wall decorations.

15. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
$278 nightly
The price is $301
Sep 14 - Sep 15
Total with taxes and fees
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

16. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
$398 nightly
The price is $398
Sep 1 - Sep 2
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
A white house with a steeply pitched roof and a small tower-like structure.

17. 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, (5 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.
$440 nightly
The price is $498
Sep 1 - Sep 2
Total with taxes and fees
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A hot tub in a backyard with a house, trees, and a clear sky.

18. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
$3,400 nightly
The price is $3,850
Oct 1 - Oct 2
Total with taxes and fees
Las Flores Villa
A patio with a round table and chairs, overlooking a body of water and a forested area during sunset.

19. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (59 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
$1,529 nightly
The price is $1,730
Sep 17 - Sep 18
Total with taxes and fees
Candlewood Lake Retreat with Private Dock
A two-story house with a deck, outdoor seating, and string lights.

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

Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Danbury
9.0 out of 10, Wonderful, (2 reviews)
"Very nice hosts and immaculately clean property. Hot tub was great. My only mention is that there isn’t actually any lake access which was misleading. We did use the hosts’ kayaks and put them on our cars to go boating which was free, but swimming is not free and about a 10 min drive away. The hosts also live above the suite (not mentioned) but we had a private entrance."
United States
Kaitlyn C.
$492 nightly
The price is $557
Sep 1 - Sep 2
Total with taxes and fees
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
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

Wyndham Southbury

Wyndham Southbury

8/10 Good
"Ok"
Wendy 1-night trip
Posted 10 hours ago
Wyndham Southbury

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 $160 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 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.