Lodging Image

Gaylordsville Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Gaylordsville holiday rentals

1. 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.
The price is NZ$355
includes taxes & fees
27 Aug - 28 Aug
Mid Century Modern Studio w/ Full Kitchen - Newly Built

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.
The price is NZ$341
includes taxes & fees
9 Sept - 10 Sept
Hoppy Hill Farm House

3. 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.
The price is NZ$223
includes taxes & fees
31 Aug - 1 Sept
Rare, peaceful glamping, hot shower, mini golf near appalachian trail

4. 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.
The price is NZ$1,268
includes taxes & fees
20 Sept - 21 Sept
Awesome Lake Home with tons of fun!

5. 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
The price is NZ$241
includes taxes & fees
1 Sept - 2 Sept
Cozy private room in a shared home with a Full-size bed and private bathroom.

6. 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.
The price is NZ$460
includes taxes & fees
31 Aug - 1 Sept
The Overlook near South Farms in Litchfield County is Hospitality, integrated.

7. 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, (19 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is NZ$733
includes taxes & fees
8 Sept - 9 Sept
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

8. 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)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is NZ$823
includes taxes & fees
27 Aug - 28 Aug
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

9. 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.
The price is NZ$2,827
includes taxes & fees
17 Sept - 18 Sept
Candlewood Lake Retreat with Private Dock

10. "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 NZ$944
includes taxes & fees
8 Sept - 9 Sept
"Country outside the city " 3 bedrooms 2 full bathrooms

11. 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 NZ$1,347
includes taxes & fees
3 Sept - 4 Sept
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

12. 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 NZ$381
includes taxes & fees
7 Sept - 8 Sept
The Perch in the Purchase -- Cozy, unique, and private

13. 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
The price is NZ$657
includes taxes & fees
31 Aug - 1 Sept
The Jefferson Guest House, Spacious, Special Views

14. 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
The price is NZ$212
includes taxes & fees
22 Sept - 23 Sept
Cozy One Bedroom Apartment Centrally Located in Southbury

15. 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.
The price is NZ$308
includes taxes & fees
29 Aug - 30 Aug
Welcome to Sweet Abby Rose!

16. 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.
The price is NZ$900
includes taxes & fees
8 Sept - 9 Sept
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots

17. Gorgeous 4-bedroom house on lovely Candlewood Lake perfect for families

Gorgeous 4-bedroom house on lovely Candlewood Lake perfect for families
Brookfield
The price is NZ$1,541
includes taxes & fees
8 Sept - 9 Sept
Gorgeous 4-bedroom house on lovely Candlewood Lake perfect for families

18. 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
The price is NZ$223
includes taxes & fees
31 Aug - 1 Sept
Glamping, family fun, pet friendly

19. 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.
The price is NZ$1,748
includes taxes & fees
17 Sept - 18 Sept
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

20. 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.
The price is NZ$238
includes taxes & fees
15 Sept - 16 Sept
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Gaylordsville Hotel Reviews

Find out more about Gaylordsville

Everything you need to know about Gaylordsville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gaylordsville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gaylordsville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gaylordsville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gaylordsville holiday rentals we have selected for you start as low as NZ$223 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gaylordsville rentals

At Expedia, we put the best Gaylordsville holiday 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 holiday.

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. 

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 3 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.