A calm lake at sunset with a silhouette of a boat and a forested hill in the background.

Chaplin Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chaplin vacation rentals

A window with a view of a grassy field and trees.

1. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (7 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
$269 nightly
The price is $305
Oct 5 - Oct 6
Total with taxes and fees
Spacious, unique barn with beautiful views.
A bedroom with a bed, a window with a curtain, a wall-mounted light, and a framed picture.

2. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.0 out of 10, Wonderful, (49 reviews)
"Very peaceful and beautiful area. Well needed relaxing time. Highly recommend! Also Host was exceptional and attentive."
United States
Melissa
$270 nightly
The price is $306
Oct 5 - Oct 6
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

3. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (19 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
$200 nightly
The price is $227
Oct 19 - Oct 20
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A wooden cabin with a balcony and stairs, surrounded by trees.

4. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful farm that’s perfect little getaway for one weekend"
United States
Justyn M.
$299 nightly
The price is $339
Oct 20 - Oct 21
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
A cozy living room with a wooden dining table, a sofa, a ceiling fan, and a view of the outdoors through a window.

5. Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Coventry
8.6 out of 10, Excellent, (13 reviews)
"Perfect place to stay when using it as a base camp to get around the are. Excellent communication from the host. She made it easy to stay there."
United States
Aaron C.
$275 nightly
The price is $312
Oct 4 - Oct 5
Total with taxes and fees
Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
A room with a wooden ceiling, a ceiling fan, a blue door, and a dining area with a table and chairs.

6. Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (47 reviews)
"Nice location, just a short walk to the water."
United States
Harris G.
$280 nightly
The price is $317
Oct 20 - Oct 21
Total with taxes and fees
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
A house with a stone chimney, a fire pit, and two Adirondack chairs in the yard.

7. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (54 reviews)
"Very cute little place to spend a weekend! My friends, partner, and I slept comfortably. The lake itself is very nice (though weather unfortunately prevented us from going out on it with the kayaks) and it is within a short drive to Hartford, UConn, and plenty of things to do. Connecticut is such a lovely state! The purpose of our trip was so that my partner and I could look at apartments in town. We were already excited to move to CT, but after this trip, we became completely confident in how...
United States
Austin R.
$278 nightly
The price is $315
Oct 4 - Oct 5
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A house with a white porch, a black door, and a window with a white frame.

8. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.0 out of 10, Wonderful, (4 reviews)
"Great spot, clean and cozy."
United States
Bud n' Mary's Marina B.
$277 nightly
The price is $314
Oct 14 - Oct 15
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
A living room with a sofa, armchair, coffee table, and a rug.

9. The Little Blue Bird · 5 Mi UConn · 2 Min I-84

The Little Blue Bird · 5 Mi UConn · 2 Min I-84
Willington
10.0 out of 10, Exceptional, (1 review)
"Great place! Great communication! Highly recommended for 1-2 people."
United States
Jeff G.
$135 nightly
The price is $152
Oct 4 - Oct 5
Total with taxes and fees
The Little Blue Bird · 5 Mi UConn · 2 Min I-84
A modern kitchen with white cabinetry, a wooden island, and a built-in stove.

10. Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 10, Good, (3 reviews)
"Great setup. Perfect crash pad for a weekend of the Natchaug Epic bike race in Thompson… slept 8 no problem. Host was helpful and beds were clean, kitchens were just what we needed"
United States
shawn c b.
$451 nightly
The price is $536
Oct 5 - Oct 6
Total with taxes and fees
Mohegan Sun Getaway Large Group Retreat
A living room with a dark gray sectional sofa, a wooden bench, a ceiling fan, and a large window with a view of trees.

11. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
9.0 out of 10, Wonderful, (8 reviews)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
$194 nightly
The price is $219
Oct 6 - Oct 7
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
An outdoor seating area with a wood-burning stove, a chair, and a view of a lake.

12. Spacious modern home on private lake

Spacious modern home on private lake
Andover
10.0 out of 10, Exceptional, (29 reviews)
"The lake house was charming, comfortable and well stocked with necessities like towels, blankets, dishes, etc"
United States
Martin G.
$349 nightly
The price is $395
Oct 12 - Oct 13
Total with taxes and fees
Spacious modern home on private lake
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

13. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
$288 nightly
The price is $326
Oct 5 - Oct 6
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Bedroom

14. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
$88 nightly
The price is $101
Oct 6 - Oct 7
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

15. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
$166 nightly
The price is $188
Oct 4 - Oct 5
Total with taxes and fees
Wizard's Roost at Underhill Hollow
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

16. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
$171 nightly
The price is $194
Oct 4 - Oct 5
Total with taxes and fees
The Tree House at Underhill Hollow
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

17. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
$166 nightly
The price is $188
Oct 4 - Oct 5
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
A dining area with a high ceiling, skylights, and a view of the outdoors.

18. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (93 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
$569 nightly
The price is $644
Nov 1 - Nov 2
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

19. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$164 nightly
The price is $183
Oct 11 - Oct 12
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
A wooden cabin with a glass upper floor, surrounded by a forest.

20. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
$244 nightly
The price is $257
Oct 4 - Oct 5
Total with taxes and fees
Dove Cabin up in the Trees
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 Chaplin Hotel Reviews

Scottish Inn Sturbridge

Scottish Inn Sturbridge

10/10 Excellent
"When traveling to and from NJ I always like to stay at the Scottish Inn in Sturbridge, MA. The staff is so nice, I always get a good nights sleep and there are restaurants within walking distance as well as a grocery store. Clean rooms, quiet, easy parking and a great cost."
Ronald 1-night trip
Posted 5 hours ago
Scottish Inn Sturbridge

Find out more about Chaplin

Everything you need to know about Chaplin 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 Chaplin 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 Chaplin vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chaplin vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chaplin. 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 Chaplin 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 $128 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 Chaplin rentals

At Expedia, we put the best Chaplin 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 Chaplin 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 Chaplin 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 Chaplin. 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 vacation rentals in Chaplin?

Yes, you can find vacation rentals close to well known attractions in Chaplin, or you can go with a more remote option if you're looking for a relaxing stay. Chaplin is known for its parks and museums.

What are some of the best vacation rentals in Chaplin?

Cozy, comfy,quiet &close to casinos: This vacation home rental outside of Chaplin is equipped with a patio, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in Chaplin?

Cultural attractions include Chaplin Museum, whereas Nickerson Park is a spot to enjoy nature. Other places in town to visit include Mansfield Hollow State Park and Beaver Brook State Park.

What’s a vacation rental in Chaplin like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Chaplin. Vacation rentals offer extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.