Cheshire Vacation Rentals

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Our top choices for Cheshire vacation rentals

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.4 out of 10, Exceptional, (17 reviews)
"Great Location - all the amenities you need for a nice restful stay. Did not have to reach-out to the host at all during our stay. "
United States
Robert S.
The price is CA $141
CA $253 total
includes taxes & fees
Apr 19 - Apr 20
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (10 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
The price is CA $789
CA $1,363 total
includes taxes & fees
Mar 26 - Mar 27
Clear LI Sound waterview, Wedding pics, Yale&Beach

6 Mi to Dtwn New Haven: Duplex w/ Shared Yard

6 Mi to Dtwn New Haven: Duplex w/ Shared Yard
3.0 star property
West Haven
The price is CA $504
CA $961 total
includes taxes & fees
Mar 26 - Mar 27
6 Mi to Dtwn New Haven: Duplex w/ Shared Yard

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
East Rock
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
Australia
Nina
The price is CA $247
CA $592 total
includes taxes & fees
Mar 26 - Mar 27
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is CA $199
CA $477 total
includes taxes & fees
Mar 26 - Mar 27
Angelica’s safe haven @ west haven

1-of-a-Kind Luxury Estate | Pool+Spa, Tennis, Pond

1-of-a-Kind Luxury Estate | Pool+Spa, Tennis, Pond
Killingworth
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful, spacious and many places to hang out"
United States
Wendy H.
The price is CA $837
CA $1,713 total
includes taxes & fees
Mar 26 - Mar 27
1-of-a-Kind Luxury Estate | Pool+Spa, Tennis, Pond

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"Clean, quiet, as advertised. "
United States
Anonymous traveller
The price is CA $232
CA $440 total
includes taxes & fees
Mar 26 - Mar 27
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale
West Haven
9.6 out of 10, Exceptional, (20 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is CA $315
CA $725 total
includes taxes & fees
Mar 26 - Mar 27
McAngel Haven: 5 mins from Yale

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful home"
United States
Glenna M.
The price is CA $172
CA $354 total
includes taxes & fees
Mar 31 - Apr 1
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
East Shore
8.8 out of 10, Excellent, (3 reviews)
"Fantastic place, amazing hosts, 100% recommend! "
United States
Zach P.
The price is CA $352
CA $704 total
includes taxes & fees
Mar 31 - Apr 1
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

#27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is CA $410
CA $801 total
includes taxes & fees
Mar 28 - Mar 29
#27- Luxury Collection

VintageGem: Prime East Rock 5 mins to Yale 5 beds

VintageGem: Prime East Rock 5 mins to Yale 5 beds
East Rock
9.4 out of 10, Exceptional, (3 reviews)
"Great time with friends."
United States
Ianaliz R.
The price is CA $247
CA $592 total
includes taxes & fees
Mar 26 - Mar 27
VintageGem: Prime East Rock 5 mins to Yale 5 beds

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is CA $302
CA $700 total
includes taxes & fees
Mar 26 - Mar 27
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!
Downtown New Haven
10.0 out of 10, Exceptional, (3 reviews)
"We loved this rental. The location is one you might not think is good BUT IT IS. I loved the location. Great coffee shop around the corner. Short walk to great restaurants and it was a safe location. I will stay here again. Also the two bedrooms with two bathrooms is rare and each bedroom with a king bed is super rare. I highly recommend this rental and Joshua was so great and helpful. "
United States
Sharla C.
The price is CA $172
CA $486 total
includes taxes & fees
Mar 26 - Mar 27
DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

Oceanfront Getaway - Quiet, Firepit + Pvt Beach

Oceanfront Getaway - Quiet, Firepit + Pvt Beach
Morgan Point
9.8 out of 10, Exceptional, (9 reviews)
"Great beach house for family vacation "
United States
david m.
The price is CA $259
CA $911 total
includes taxes & fees
Mar 31 - Apr 1
Oceanfront Getaway - Quiet, Firepit + Pvt Beach

Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (70 reviews)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
The price is CA $121
CA $246 total
includes taxes & fees
Mar 29 - Mar 30
Spacious 2 Bedroom apartment close to Yale Bowl

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
9.8 out of 10, Exceptional, (26 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is CA $823
CA $1,331 total
includes taxes & fees
Apr 1 - Apr 2
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Spacious Victorian Loft

Spacious Victorian Loft
West New Haven
9.6 out of 10, Exceptional, (21 reviews)
"Great place! Bigger than expected and great location for exploring the central New Haven area."
United States
Anna A.
The price is CA $216
CA $429 total
includes taxes & fees
Mar 26 - Mar 27
Spacious Victorian Loft

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (63 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is CA $428
CA $719 total
includes taxes & fees
Apr 21 - Apr 22
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

The Jewel of The Cove - Historic Coastal Retreat

The Jewel of The Cove - Historic Coastal Retreat
East Shore
9.8 out of 10, Exceptional, (7 reviews)
"This was a great place to stay in New Haven, and a lot of care has gone into making it a welcoming house."
United States
Geoffrey H.
The price is CA $284
CA $712 total
includes taxes & fees
Mar 31 - Apr 1
The Jewel of The Cove - Historic Coastal Retreat
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 Cheshire Hotel Reviews

Find out more about Cheshire

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cheshire. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we have vacation rentals in Cheshire close to Cheshire Hollow Farm, or you can select a more remote option if you'd like a relaxing place to stay. Our travelers say Cheshire has a good selection of restaurants. Make sure you have time to check out the waterfalls and shopping during your trip.

What are some of the best vacation home rentals in Cheshire?

Oceanfront Getaway - Quiet, Firepit + Pvt Beach: Visitors like this Cheshire vacation home rental. It is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease 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.

What’s there to see and do in Cheshire?

Family-friendly attractions include Cheshire Hollow Farm and Barker Character, Comic and Cartoon Museum, whereas Roaring Brook Park and Drazen Orchards are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Bartlem Park are other places worth a visit.

What’s a vacation rental in Cheshire like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Cheshire. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.