We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday villas in Cheshire, CT

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 20 Rentals in the Cheshire Area
loading...
Sort by

The following rentals are within 30 kilometers of Cheshire, Connecticut.

From
€131
Per Night
View Details
1 / 27
Payment Protection
Southbury
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
From
€308
Per Night
View Details
1 / 14
Payment Protection
Guilford
2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
From
€151
Per Night
View Details
1 / 19
New Haven
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (6) Make Enquiry
From
€220
Per Night
View Details
1 / 15
Guilford
4 Bedrooms, 1 Bathroom, Sleeps 8
Details Reviews (3) Make Enquiry
Amenities & Details
  • Fireplace
  • Grill
  • Internet Access
  • Ocean Views
  • Private Fishing...
  • Waterfront
  • Water Views
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
We love our cottage and you will too! 'Seacliff,' a classic turn of the century cedar shingled beach cottage, is located in the quiet Guilford, CT community of Mulberry Point. Direct water access for swimming, beachcombing, kayaking and fishing plus family-friendly association beach within a... View all property information
Make Enquiry
5 of 5 stars Reviewed 20 September 2014
If you are looking for an almost indescribably beautiful setting and a rustic, relaxing location, Seacliff is it. The view from the front screen porch and terrace is nothing short...
See all reviews
From
€115
Per Night
View Details
1 / 15
Payment Protection
Branford
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (11) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This newly renovated one bedroom cottage is set in the midst of other cottages. With a private back garden, patio, beautiful flowers, and steps from a private neighborhood beach , the cottage is clean, and comfortable. For cool nights there is a gas fire, and an air conditioner in the bedroom... View all property information
Make Enquiry
5 of 5 stars Reviewed 3 August 2014
Last January we had set our eyes on the Ennis Cottage for the last two weeks of July and the long wait was worth it. For spending a holiday there is like uncorking your first...
5 of 5 stars Reviewed 21 April 2013
We had a very pleasant stay at the Ennis Cottage. The warm welcome we felt with Ron and his help getting around in and near Branford made us feel home and looking forward to...
See all reviews
From
€220
Per Night
View Details
1 / 38
Payment Protection
Guilford
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
we have over 30 POSITIVE REVEIWS ON HOMEAWAY 'We had a wonderful time at this lovely home in Guilford. We found the home to be cozy, comfortable and beautifully decorated. We will definitely stay here again in the future. We loved being able to walk to town to the Green, shoppes, restaurants, etc.... View all property information
Make Enquiry
3 of 5 stars Reviewed 8 December 2014
The house is in a great location and has good bones. It was generally what we needed, though it lacked some basic things like sheets that fit the bed and bath towels. Some basic...
See all reviews
From
€110
Per Night
View Details
1 / 12
Payment Protection
Guilford
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This is a great getaway, easy from NYC, to Guilford, a beautiful shoreline town 18 miles East of New Haven. The house is a 30 minute walk to the train or a 10 minutes stroll to the historic village green, coffee shops, restaurants, a great bookstore and chocolatier. The house, built in 1870, by a... View all property information
Make Enquiry
From
€163
Per Night
View Details
1 / 10
Payment Protection
Wallingford
1 Bedroom, 2 Bathrooms, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Welcome to The Wallingford Victorian Inn We are a B&B The room rate posted is for one suite that will sleep 2 We have 5 suites available for rental if your party is larger The rate is per suite per night The Wallingford Victorian Inn regally presides over the corners of North Main Street and... View all property information
Make Enquiry
From
€66
Per Night
View Details
1 / 20
Payment Protection
Hamden
1 Bedroom, 1 Bathroom, Sleeps 3
Booking
Details Make Enquiry
Amenities & Details
  • Grill
  • Internet Access
  • Mountain Views
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • x
About this property
Beautiful, modern, clean, SAFE, comfortable, and convenient to all transportation and highways. This stunner has a warm, inviting atmosphere with a hostess who is knowledgable about Connecticut AND New York City. The rental is a HIP, bright, basement apartment in a well appointed Colonial style... View all property information
Make Enquiry
From
€44
Per Night
View Details
1 / 15
Payment Protection
Plymouth
8 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This beatuiful 8 room Raised Ranch is located on a quiet dead end street. Home is very spacious with a new efficient oil based heating system. Large eat in kitchen with appliances. Large dining room with sliders to two tier deck overlooking a 1 acre lot. Living room is large with fireplace.... View all property information
Make Enquiry
Get the List
From
€264
Per Night
View Details
1 / 15
Haddam
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Secluded behind a stand of tall pines, the Laurel Cottage has been restored and expanded to include a full kitchen, bathroom with double pedestal bathtub and a large subway tiled shower. A cozy double brass bed in the Great Room and a luxurious pull out queen size bed on the all season porch... View all property information
Make Enquiry
From
€159
Per Night
View Details
1 / 11
Payment Protection
Portland
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Sauna
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
One bedroom, furnished, deluxe condo in the core of Portland, Oregon…with fantastic views of the West Hills, PSU, and Downtown Portland. The condo is just East of the Portland State University Campus. Rented on a month by month basis. Convenient to all aspects. Attributes: √ Near the top of the... View all property information
Make Enquiry
From
€264
Per Night
View Details
1 / 16
Payment Protection
Bethlehem
6 Bedrooms, 4 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Gym
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All... View all property information
Make Enquiry
From
€881
Per Night
View Details
1 / 10
Payment Protection
Branford
5 Bedrooms, 5 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Two acres of private New England charm over looking the Thimble Islands. Set atop a hill with a large rolling lawn perfect for all types of family lawn games.The vintage shingle stone home was built in 1932 for a wealthy Connecticut family. They created a sandy beach that rivals the size of the... View all property information
Make Enquiry
From
€220
Per Night
View Details
1 / 16
Payment Protection
Woodbury
3 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
This antique-filled, light-splashed colonial two story home on Connecticut's Antique Trail has spacious indoor and outdoor lounging areas in a beautiful one acre private garden setting three minutes from Woodbury's historic town center. The home was a former bed and breakfast property and has all... View all property information
Make Enquiry
From
€198
Per Night
View Details
1 / 11
Payment Protection
Wallingford
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Brae Cottage is an elegantly designed small home. It sits in an open field, next to woods and overlooking a pond. There is a large living room with cathedral ceiling and fireplace. The living room opens onto a covered terrace and includes a queen sized Murphy Bed. There is fully equipped kitchen &... View all property information
Make Enquiry
From
€260
Per Night
View Details
1 / 12
Payment Protection
Branford
Studio, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
From generous picture windows enjoy views of Long Is. Sound and quaint Thimble Islands dotted with simple cottages and mansions. Large front room with a small kitchen hidden in a a 1930's armoire. A round dining table is lite from a 60' chandelier fit for a castle. Created by a professional... View all property information
Make Enquiry
From
€286
Per Night
View Details
1 / 39
Middle Haddam
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Captain's House, a 3,400 SF 3-level renovated waterfront Victorian, features 5 bedrooms, 3-1/2 baths, gourmet kitchen,wraparound deck, tennis court and 40' dock. A magical place to relax & recharge... Knowles Landing is one of the most beautiful waterfront estates on the Connecticut River.... View all property information
Make Enquiry
From
€881
Per Night
View Details
1 / 3
Farmington
6 Bedrooms, 8 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Fireplace
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
magnificant French Normandy hillside all brick 6 bedroom 7.5 bath custom Mansion with 3.5 acres beautiful, lush, private, exclusive ESTATE, in prestigious FARMINGTON, CT. Just at I-84, Exit 39. May be leased for long weekends, weekly or long term stay. . 6 bedrooms, 7.5 baths, swimming pool,... View all property information
Make Enquiry
From
€57
Per Night
View Details
1 / 7
Payment Protection
Bristol
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Located in 1880 home in older quiet neighborhood .Nearby park to walk in. Located 2 miles from ESPN and the great Lake Compounce amusement park. Walking distance to clock museum, shopping, library and churches. Short drive to carousel museum. 13 miles from capital of Hartford. Off street... View all property information
Make Enquiry
Go to map view
Book Online(15)
Use filters to find the best results!

Suitability

  • Wheelchair access (1)
  • Elder access (8)
  • Suitable for children (3)
  • Pet friendly (5)
  • Smoking allowed (0)

Amenities

  • Internet (17)
  • Other outdoor space (17)
  • Air Conditioning (15)
  • Parking (15)
  • Grill (13)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities