Chaplin Holiday Rentals
House
- Mystic - New London
- ·
- Baltic
- 0.69 mi to center
10.0Exceptional
(23 Reviews)
2 Bedrooms
1 Bath
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
£149/Night
7 Nights - £1,042
House
- Connecticut
- ·
- Mansfield Depot
- 1.63 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399.31 ft²
- Parking
Pool
Internet
Pet Friendly
£187/Night
7 Nights - £1,309
House
- Willington
- ·
- Mansfield
- 0.71 mi to center
8.8Fabulous
(126 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£192/Night
7 Nights - £1,345
House
- Mystic - New London
- ·
- Baltic
- 0.30 mi to center
10.0Exceptional
(19 Reviews)
1 Bedroom
1 Bath
4 Guests
Hot Tub- Parking
- Air Conditioner
- Internet
£215/Night
7 Nights - £1,504
House
- Willington
- ·
- Coventry Lake
- 0.41 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
6 Guests
1205.56 ft²
- Parking
- Internet
Child Friendly
Sports/Activities
£319/Night
7 Nights - £2,232
House
- Mystic - New London
- ·
- Baltic
- 0.16 mi to center
10.0Exceptional
(25 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£662/Night
7 Nights - £4,635
Cottage
- Willington
- ·
- Ashford
- 3.35 mi to center
10.0Exceptional
(95 Reviews)
2 Bedrooms
1 Bath
4 Guests
812 ft²
- Parking
Ocean View- Balcony/Terrace
View
£159/Night
7 Nights - £1,116
House
- Connecticut
- ·
- Mansfield Depot
- 1.51 mi to center
10.0Exceptional
(85 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
£327/Night
7 Nights - £2,292
Cottage
- Willington
- ·
- Ashford
- 2.15 mi to center
10.0Exceptional
(53 Reviews)
2 Bedrooms
1 Bath
8 Guests
1200 ft²
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
£306/Night
7 Nights - £2,138
Luxury Holiday Rentals in Chaplin
Over 104+ Luxury Holiday Rentals in or Near Chaplin
House
- Willington
- ·
- Coventry Lake
- 0.95 mi to center
10.0Exceptional
(10 Reviews)
5 Bedrooms
5 Baths
15 Guests
5746 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
£1,497/Night
7 Nights - £10,482
House
- Willington
- ·
- Coventry Lake
- 0.44 mi to center
10.0Exceptional
(40 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£1,459/Night
7 Nights - £10,216
House
- Woodstock
- ·
- South Woodstock
- 0.95 mi to center
10.0Exceptional
(27 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
£545/Night
7 Nights - £3,814
House
- Willington
- ·
- Woodstock Valley
- 1.11 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
1300 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
£516/Night
7 Nights - £3,614
House
- Willington
- ·
- Mansfield Center
- 1.43 mi to center
10.0Exceptional
(8 Reviews)
5 Bedrooms
3 Baths
7 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
£462/Night
7 Nights - £3,234
House
- Willington
- ·
- Ashford
- 3.41 mi to center
10.0Exceptional
(24 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£458/Night
7 Nights - £3,207
House
- Connecticut
- ·
- Pomfret
- 1.05 mi to center
7 Bedrooms
7 Baths
14 Guests
5500.36 ft²
- Parking
- Internet
- Child Friendly
Wheelchair Accessible
£428/Night
7 Nights - £2,997
House
- Willington
- ·
- Willimantic
- 0.42 mi to center
9.8Exceptional
(18 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
£379/Night
7 Nights - £2,654
Cottage
- Willington
- ·
- Coventry Lake
- 0.41 mi to center
10.0Exceptional
(21 Reviews)
3 Bedrooms
1 Bath
6 Guests
1200 ft²
- Parking
- View
- Kitchen
- Air Conditioner
£373/Night
7 Nights - £2,608
Top-Rated Holiday Rentals with a Pool in Chaplin
Over 8+ The Best Private Villas and Holiday Rentals in Chaplin with a Pool
House
- Connecticut
- ·
- Canterbury
- 3.63 mi to center
9.8Exceptional
(9 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
£136/Night
7 Nights - £949
House
- Connecticut
- ·
- Columbia
- 1.90 mi to center
8.8Fabulous
(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
5000 ft²
Private Pool- Hot Tub
- Parking
- Pool
£301/Night
7 Nights - £2,111
Hotel
- Willington
- ·
- Mansfield Center
- 2.01 mi to center
8.0Excellent
(1006 Reviews)
1 Bath
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
£143/Night
7 Nights - £1,003
Hotel
- Connecticut
- ·
- Willington
- 2.75 mi to center
4.2Average
(1006 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Balcony/Terrace
£63/Night
7 Nights - £443
House
- Willington
- ·
- Coventry Lake
- 0.46 mi to center
10.0Exceptional
(41 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
£219/Night
7 Nights - £1,534
Cabin
- Willington
- ·
- Ashford
- 0.49 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
£258/Night
7 Nights - £1,804
Cabin
- Willington
- ·
- Ashford
- 0.49 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£153/Night
7 Nights - £1,073
Bed & Breakfast
- Connecticut
- ·
- Rogers
- 1.53 mi to center
9.4Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
£154/Night
7 Nights - £1,081
Pet-Friendly Holiday Rentals in Chaplin
Over 33+ Pet-Friendly Holiday Rentals in or Near Chaplin
Cottage
- Connecticut
- ·
- Mansfield Depot
- 1.63 mi to center
10.0Exceptional
(35 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£236/Night
7 Nights - £1,654
Bed & Breakfast
- Connecticut
- ·
- Pomfret
- 3.37 mi to center
9.6Exceptional
(46 Reviews)
1 Bedroom
1 Bath
4 Guests
645.83 ft²
- Breakfast
EV Charge Station- Parking
- Balcony/Terrace
£165/Night
7 Nights - £1,155
Cottage
- Willington
- ·
- Hampton Hill Historic District
- 0.41 mi to center
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£313/Night
7 Nights - £2,188
Cottage
- Willington
- ·
- Coventry Lake
- 0.99 mi to center
10.0Exceptional
(28 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£343/Night
7 Nights - £2,399
House
- Willington
- ·
- Hampton Hill Historic District
- 0.41 mi to center
9.5Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
1506.95 ft²
- Parking
Spa
Skiing- View
£189/Night
7 Nights - £1,320
Cottage
- Connecticut
- ·
- Windham
- 0.30 mi to center
10.0Exceptional
(28 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
£190/Night
7 Nights - £1,328
House
- Willington
- ·
- Ashford
- 3.38 mi to center
9.6Exceptional
(35 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£173/Night
7 Nights - £1,213
House
- Willington
- ·
- Hampton
- 1.50 mi to center
9.6Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Air Conditioner
- Internet
- Pet Friendly
Laundry
£194/Night
7 Nights - £1,357
Cottage
- Willington
- ·
- Coventry Lake
- 0.71 mi to center
9.4Exceptional
(29 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
£156/Night
7 Nights - £1,091
Large Holiday Rentals and Private Villas in Chaplin
Over 6+ Large Holiday Rentals and Private Villas in or Near Chaplin
House
- Connecticut
- ·
- Columbia
- 1.63 mi to center
8.0Excellent
(10 Reviews)
5 Bedrooms
2 Baths
9 Guests
- Air Conditioner
- Internet
- Laundry
Bedding/Linens
£330/Night
7 Nights - £2,311
New
House
- Willington
- ·
- Hampton
- 2.02 mi to center
3 Bedrooms
2 Baths
14 Guests
4000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£363/Night
7 Nights - £2,543
House
- Connecticut
- ·
- Pomfret
- 1.03 mi to center
6.8Good
(11 Reviews)
7 Bedrooms
7 Baths
14 Guests
5294 ft²
- Hot Tub
- Parking
- Skiing
- Balcony/Terrace
£488/Night
7 Nights - £3,418
Apartment
- Willington
- ·
- Willimantic
- 0.65 mi to center
3 Bedrooms
1 Bath
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£106/Night
7 Nights - £740
House
- Connecticut
- ·
- Lebanon
- 2.18 mi to center
5.0Average
(1 Review)
5 Bedrooms
3 Baths
14 Guests
- Kitchen
- Internet
- Child Friendly
- Laundry
£262/Night
7 Nights - £1,832
House
- Connecticut
- ·
- Pomfret
- 1.05 mi to center
3.3Average
(3 Reviews)
7 Bedrooms
7 Baths
14 Guests
5500 ft²
- Kitchen
- Air Conditioner
- Internet
- Bedding/Linens
£501/Night
7 Nights - £3,505
Wheelchair Accessible Holiday Homes in Chaplin
Over 4+ Wheelchair Accessible Holiday Homes in or Near Chaplin
Hotel
- Willington
- ·
- Storrs
- 0.19 mi to center
9.0Exceptional
(306 Reviews)
1 Bath
467.46 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
£226/Night
7 Nights - £1,580
Hotel
- Willington
- ·
- Storrs
- 0.21 mi to center
9.6Exceptional
(1001 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
£171/Night
7 Nights - £1,196
Hotel
- Connecticut
- ·
- Brooklyn
- 2.41 mi to center
9.0Exceptional
(192 Reviews)
3 Baths
322.92 ft²
- Parking
- View
- Air Conditioner
- Internet
£81/Night
7 Nights - £564
Hotel
- Connecticut
- ·
- Willington
- 2.75 mi to center
3.6Average
(87 Reviews)
1 Bath
1422.18 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
£49/Night
7 Nights - £345
Chaplin Private Villas and Holiday Homes Under $200
Over 17+ Chaplin Private Villas and Holiday Homes Under $200
Apartment
- Willington
- ·
- Coventry Lake
- 0.71 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
£104/Night
7 Nights - £729
House
- Connecticut
- ·
- Canterbury
- 3.63 mi to center
7.0Very Good
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
1001.04 ft²
- Parking
- Balcony/Terrace
- Internet
- Sports/Activities
£119/Night
7 Nights - £835
Hotel
- Connecticut
- ·
- Brooklyn
- 2.41 mi to center
9.2Exceptional
(903 Reviews)
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£84/Night
7 Nights - £591
House
- Willington
- ·
- Storrs
- 1.25 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
3 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
£62/Night
7 Nights - £431
Apartment
- Willington
- ·
- South Coventry
- 0.19 mi to center
2 Bedrooms
1 Bath
6 Guests
699.65 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
£138/Night
7 Nights - £968
House
- Connecticut
- ·
- Brooklyn
- 2.62 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£55/Night
7 Nights - £385
Apartment
- Willington
- ·
- Coventry Lake
- 0.56 mi to center
9.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
625 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
£85/Night
7 Nights - £595
House
- Willington
- ·
- Willimantic
- 1.03 mi to center
2.0Average
(1 Review)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£98/Night
7 Nights - £687
House
- Connecticut
- ·
- Woodstock
- 3.15 mi to center
9.8Exceptional
(14 Reviews)
3 Bedrooms
1 Bath
6 Guests
1300 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
£146/Night
7 Nights - £1,019
Instantly Bookable Holiday Homes in Chaplin
Over 36+ Instantly Bookable Holiday Homes in or Near Chaplin
House
- Willington
- ·
- Coventry Lake
- 0.31 mi to center
10.0Exceptional
(22 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£188/Night
7 Nights - £1,317
Cottage
- Connecticut
- ·
- Pomfret
- 2.43 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
698 ft²
- Air Conditioner
- Internet
- Child Friendly
- Laundry
£230/Night
7 Nights - £1,610
New
Apartment
- Connecticut
- ·
- Mansfield Depot
- 1.61 mi to center
9.8Exceptional
(18 Reviews)
1 Bedroom
2 Baths
4 Guests
900 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
£226/Night
7 Nights - £1,580
Apartment
- Connecticut
- ·
- Willington
- 1.90 mi to center
9.8Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£193/Night
7 Nights - £1,348
Cabin
- Connecticut
- ·
- Willington
- 1.90 mi to center
9.4Exceptional
(36 Reviews)
1 Bedroom
1 Bath
4 Guests
250 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£247/Night
7 Nights - £1,731
Apartment
- Willington
- ·
- South Coventry
- 0.19 mi to center
9.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
6 Guests
700 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
£212/Night
7 Nights - £1,481
Cabin
- Willington
- ·
- Coventry Lake
- 0.96 mi to center
8.8Fabulous
(52 Reviews)
2 Bedrooms
1 Bath
6 Guests
764 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£256/Night
7 Nights - £1,795
New
House
- Willington
- ·
- Coventry Lake
- 0.36 mi to center
2 Bedrooms
1 Bath
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
£244/Night
7 Nights - £1,706
House
- Willington
- ·
- Storrs
- 0.68 mi to center
10.0Exceptional
(13 Reviews)
3 Bedrooms
1 Bath
6 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£224/Night
7 Nights - £1,565
Book a Last Minute Place to Stay in Chaplin
About Casai's Private Villas and Holiday Rentals in Chaplin
Discover more than 113 vacation rentals available in Chaplin. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chaplin.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chaplin, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chaplin. On average, places to stay near Chaplin offer 794.01 ft², with nightly prices averaging £291.
With Casai, finding and comparing holiday rentals in Chaplin is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Chaplin
| Type | Count |
|---|---|
| Vacation Homes | 63 |
| Cottages | 15 |
| Holiday Apartments | 11 |
Use these Quick Filters to Find a Holiday Rental in Chaplin
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Chaplin.
Weather in Chaplin, CT
View the weather forecast for Chaplin before booking your Chaplin Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Chaplin, CT
Casai offers a large selection of top attractions around Chaplin . Research things to do on your vacation before you visit Chaplin.
Other Places to Stay in Chaplin, CT
Frequently Asked Questions About Chaplin?
What are the top holiday rentals in Chaplin?
With numerous options available in Chaplin, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chaplin:
- Charming Lakefront Cottage
- The Bungalow at Eagleville Lake Under 3 miles to UCONN!
- Magical Waterfront Cottage! Pet friendly!
- Updated Lakefront House *outdoor tv and water toys- 10 min from UConn
- Lakefront Connecticut Retreat Near UConn
- Lake Getaway at Coventry Lake! close to Uconn
- Cozy 1-bedroom cottage with WiFi, AC in charming Windham
- Stunning Lakefront Escape! Book Your Dream Getaway!
- Hanover Vineyards
- Beautiful lake front home. Amazing view!
Which holiday homes in Chaplin are best for families?
If you're searching for a family-friendly holiday home in Chaplin, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chaplin:
- Cabin Love at the Lake
- Cozy Rural Guest House: Close to Wedding Venues
- Charming 3-bedroom Lakehouse in Columbia with water views and dock
How many Casai.uk holiday rentals are available in Chaplin?
As of 2026, Casai boasts over 113 properties listed in the Chaplin area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chaplin.
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