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Gaylordsville Holiday Rentals

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Holiday Rentals in Gaylordsville

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.2 out of 10, Wonderful, (15)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.2 out of 10, Wonderful, (35)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (82)
"The house was super clean and very easy to take care of while we were here. It was perfect for a remote getaway, hiking and just being quiet. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Magnificent Lake View

2.0 star property
Magnificent Lake View

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (25)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

10.0 out of 10, Exceptional, (122)
"My family and I stayed at the Lake House for the holiday. We can not say enough about the amenities, the house & the owners. We look forward to returning to this magical place for our next family reunion."
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very good, (2)
"The host was very kind and responsive, which we truly appreciated. However, the house was not properly cleaned. There were a lot of flies inside, the basement had a strong musty smell, and the hot tub water was untreated and had a bad odor, With better cleaning, maintenance, and care for the house the stay could have been much more pleasant."
Spacious Woodbury Home w/ Pool + Hot Tub!

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.2 out of 10, Wonderful, (24)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Awesome Lake Home with tons of fun!

2.0 star property
The price is AU$1,177
includes taxes & fees
30 July - 31 July
Awesome Lake Home with tons of fun!

New One Bedroom Apartment Centrally Located in Southbury

9.8 out of 10, Exceptional, (6)
"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "
The price is AU$206
includes taxes & fees
29 July - 30 July
New One Bedroom Apartment Centrally Located in Southbury

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
The price is AU$1,110
includes taxes & fees
30 July - 31 July
CT Gate House Goshen CT, Gate House Goshen CT

Spectacular Lake front house

9.6 out of 10, Exceptional, (4)
Spectacular Lake front house

Twin Cedar Pond: Lovely Farmhouse w/ Sprawling Deck and Therapy Pool

10.0 out of 10, Exceptional, (10)
"We had some trouble with our check in process, but the response time to fix it was quick. The hot tub was lovely, and the pool house was so fun for both the adults and the kids. There was an issue with my wife finding old kids applesauce packets behind the couch throw pillow. Other than that it was a great stay. Kids had fun on the swings and hammock."
Twin Cedar Pond: Lovely Farmhouse w/ Sprawling Deck and Therapy Pool

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (17)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

10.0 out of 10, Exceptional, (79)
"We stayed for a birthday weekend with a few other couples and had a great time. There is plenty of space for everyone to spread out and each 'area' of the house is incredibly comfortable (especially the movie theater). If you need anything there are plenty of stores close by and the area is very safe. Overall, no complaints and would recommend to anyone looking for a getaway."
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

My favorite place!

2.0 star property
2.0 out of 10, (1)
My favorite place!

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (43)
"Had an amazing stay. House was stocked with all of the essentials. Fantastic location. Would definitely stay again!"
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

9.6 out of 10, Exceptional, (86)
"We had an amazing time. The house was beautiful and clean and communication between us and the hosts was wonderful. We would love to stay there again!"
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

9.6 out of 10, Exceptional, (14)
"We really enjoyed being able to stay at such a beautiful home. Between the animals and the hot tub view - the serenity will be hard to match elsewhere!"
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
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

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, King Bed, 1 Hour & 15 Min from NYC etc!: This holiday home rental outside of Gaylordsville is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Gaylordsville?

Choose from 4 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.