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Gaylordsville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Gaylordsville vacation rentals

Private kitchen

1. 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
10.0 out of 10, Exceptional, (1 review)
"Clean and close to activitys"
United States
randall
$127 nightly
The price is $144
Oct 4 - Oct 5
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
Smart TV, fireplace, books

2. 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, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
$216 nightly
The price is $245
Sep 25 - Sep 26
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Property grounds

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

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
$310 nightly
The price is $352
Oct 18 - Oct 19
Total with taxes and fees
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Exterior

4. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
$108 nightly
The price is $121
Sep 27 - Sep 28
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

5. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
$683 nightly
The price is $776
Sep 23 - Sep 24
Total with taxes and fees
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
Interior

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 23 - Sep 24
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
1 bedroom, internet, bed sheets

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 23 - Sep 24
Total with taxes and fees
Welcome to Sweet Abby Rose!
Outdoor dining

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, (4 reviews)
"Lovely private & secluded spot for a solo traveler or a couple. Spotlessly clean, very quiet, convenient to town for restaurants.Loved the deck & the stocked kitchen.Jenny & TJ were great hosts. Check-in was easy & communication was great."
United States
Linda E.
$204 nightly
The price is $231
Sep 29 - Sep 30
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
Coffee/tea maker, fridge, microwave, oven

9. "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.
$505 nightly
The price is $571
Sep 30 - Oct 1
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
TV, fireplace, books

10. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (4 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.
$487 nightly
The price is $552
Sep 30 - Oct 1
Total with taxes and fees
The Little Lake Cabin with hot tub
Interior

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

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
$256 nightly
The price is $277
Sep 23 - Sep 24
Total with taxes and fees
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
TV, fireplace

12. 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.
$369 nightly
The price is $400
Oct 5 - Oct 6
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Exterior

13. 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.
$247 nightly
The price is $279
Sep 23 - Sep 24
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Interior

14. 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, (17 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
$243 nightly
The price is $275
Sep 27 - Sep 28
Total with taxes and fees
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Marina

15. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (8 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
$927 nightly
The price is $1,051
Sep 27 - Sep 28
Total with taxes and fees
North Cliff House - Private Dock & Sauna
Exterior

16. 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
9.8 out of 10, Exceptional, (6 reviews)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
$434 nightly
The price is $491
Sep 23 - Sep 24
Total with taxes and fees
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Property grounds

17. 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.
$610 nightly
The price is $691
Oct 18 - Oct 19
Total with taxes and fees
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Exterior

18. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
$3,348 nightly
The price is $3,850
Oct 1 - Oct 2
Total with taxes and fees
Las Flores Villa
Coffee/tea maker, fridge, microwave, oven

19. 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
$393 nightly
The price is $393
Sep 28 - Sep 29
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
Interior

20. 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
Sep 27 - Sep 28
Total with taxes and fees
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
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

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

10/10 Excellent
"Easy check in. Helpful young woman at front desk. Super comfy beds and pillows. Quiet room. Very good coffee. 😊 We did not stay for breakfast but we have at other express holiday inns and they were good."
Priscilla 1-night trip
Posted 6 hours ago
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

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 $185 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.