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Compare 255 Vacation Homes in Middlefield with updated reviews, rates, and availability.

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (86)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
The price is AED 551
AED 1,591 total
includes taxes & fees
23 Dec - 24 Dec
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Charming beach home, complete with pool & cozy guest house!
Exterior

Charming beach home, complete with pool & cozy guest house!

9.6 out of 10, Exceptional, (23)
"Wonderful property. Plenty of room for 7 adults. Would definitely stay there again. "
Charming beach home, complete with pool & cozy guest house!
Family Gem on Dyer Street

Family Gem on Dyer Street

10.0 out of 10, Exceptional, (2)
"Needed a place to stay for the night and it was just the perfect spot. The house was just as it seemed online and it was a lot bigger than I expected. Everything was really nice and the host was super nice and very easy to communicate with. Would 100% recommend to others for their next stay."
The price is AED 804
AED 1,543 total
includes taxes & fees
16 Jan - 17 January 2025
Family Gem on Dyer Street
15mins to Hartford, Home in Manchester w/ King Bed
Exterior

15mins to Hartford, Home in Manchester w/ King Bed

2.0 star property
7.0 out of 10, Good, (2)
"We stay in rental all the time. This was definitely the worst that we have ever seen. There was no booklet of information left to give you instructions for the house. There were no labels on switches, instructions on how to use the fireplace, photograph of the supplies in the kitchen were not the same as what you Experienced. Made it very difficult to cook, so we just didn’t. The pots and pans were old and scratched, and not the kind of thing that anybody should be using and they should be...
The price is AED 687
AED 1,348 total
includes taxes & fees
19 Dec - 20 Dec
15mins to Hartford, Home in Manchester w/ King Bed
Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River
Back Patio-Pool, Hot tub, Fireplace, firepit, Bar & TV, Bathroom, Outdoor Shower

Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River

10.0 out of 10, Exceptional, (31)
"We stayed for our annual Columbus Day weekend away with a group of 9 friends. The house was very comfortable and we had plenty of space. We really enjoyed the game room in the evenings - all the games were in excellent condition and everything was in working order (which has not usually been the case at other vacation rentals we have been to). We were lucky enough to have beatiful fall weather all weekend, so we could enjoy the lovely back yard. We made use of the gas grill, watch a playoff game...
Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River
Home on the sound
Room

Home on the sound

8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound
Enjoy a taste of New England in Historic Guilford Ct
Property grounds

Enjoy a taste of New England in Historic Guilford Ct

10.0 out of 10, Exceptional, (9)
"Wonderful property combining original details with modern amenities. Well located near the town green and shops. We would definitely stay here again."
Enjoy a taste of New England in Historic Guilford Ct
146 Raymond · Prime West Hartford Center: Timeless Charm
kitchen

146 Raymond · Prime West Hartford Center: Timeless Charm

10.0 out of 10, Exceptional, (10)
"Great old West Hartford home. Very convenient to Center activities for us this weekend. Owner great to deal with. Highly recommended."
146 Raymond · Prime West Hartford Center: Timeless Charm
Ranch style living at its best with country garden & patio!
Room

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (8)
"Host worked with me due to larger dog. Very accurate instructions and all amenities were very good. Will stay here again"
Ranch style living at its best with country garden & patio!
Near Yale 8 beds Gaming Room
Exterior

Near Yale 8 beds Gaming Room

The price is AED 1,969
AED 3,957 total
includes taxes & fees
2 Jan - 3 January 2025
Near Yale 8 beds Gaming Room
Luxe Lake House in Connecticut
Sun Room

Luxe Lake House in Connecticut

The price is AED 1,080
AED 3,391 total
includes taxes & fees
13 Jan - 14 January 2025
Luxe Lake House in Connecticut
Cozy 4 Bedroom West Hartford House
Living area

Cozy 4 Bedroom West Hartford House

2.0 star property
Cozy 4 Bedroom West Hartford House
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Living area

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
10.0 out of 10, Exceptional, (1)
"Enjoyed one night in this 3Br property. It was comfortable, secure and easy to locate. Great parking, kitchen, tv and wash/dry facilities. Would recommend."
The price is AED 687
AED 1,348 total
includes taxes & fees
19 Dec - 20 Dec
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Walk to Beaches: Sunny East Haven Home w/ Grill
East Haven Vacation Rental | 4BR | 1.5BA | 1,520 Sq Ft | Stairs Required

Walk to Beaches: Sunny East Haven Home w/ Grill

2.0 star property
10.0 out of 10, Exceptional, (3)
"6 of us stayed here for a music festival. The location, fantastic! Ocean views, check. The bedding, the furniture, kitchen supplies....no amenity was overlooked. Happened to meet owner when were checking in. He was great. Couldn't have been more accomodating. Great great place for a few nights or longer. Wush we were here longer. "
Walk to Beaches: Sunny East Haven Home w/ Grill
Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!
Exterior

Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

2.0 star property
10.0 out of 10, Exceptional, (6)
"We had an absolute fantastic time staying at this place. My son was got married at the Beech Tree Cottages (also was the perfect wedding venue) in Madison, Ct. about 15 minutes from the house which worked out perfectly for staying here. From start to finish, everything exceeded our expectations. The communication with Chase was smooth and prompt, making the booking process hassle free. Upon our arrival we were greeted with a welcome gift. The space was clean, modern and beautifully...
Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!
Cozy Coastal Getaway
Private kitchen

Cozy Coastal Getaway

2.0 star property
10.0 out of 10, Exceptional, (1)
"My daughter and I recently spent four wonderful nights at this incredible home, and we couldn't have been happier. It was cozy, impeccably clean, and the hosts were very responsive. The location was perfect—just halfway to the water and two blocks from the charming Guilford Green. It’s a beautiful area, perfect for walking or running. The hosts went above and beyond by providing thoughtful touches like B&BW toiletries, high-quality linens, coffee, and essential cooking ingredients. We truly...
Cozy Coastal Getaway
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Exterior image

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Cozy newly remodeled home close to major amenities in Connecticut a
Living room

Cozy newly remodeled home close to major amenities in Connecticut a

8.4 out of 10, Very Good, (16)
"I love staying here. Each visit I bring something new from Louisiana and leave it for the next guest. The cooking supplies are admirable for a home, and especially so for a home away-from-home. We couldn't find a better place to stay. The beds are super comfy, though the furniture requires extra padding. Fortunately there are lots of blankets to use as cishioning."
Cozy newly remodeled home close to major amenities in Connecticut a
Direct Waterfront Private Beach Escape
Room

Direct Waterfront Private Beach Escape

9.8 out of 10, Exceptional, (12)
"The house was great! Beautiful ocean front property with beachy vibes all throughout the neighborhood and interior of the home. The host was extremely clear on directions and provided amazing instructions. Very comfortable stay! "
Direct Waterfront Private Beach Escape
Charming Coastal Retreat Steps from the Beach!
Living area

Charming Coastal Retreat Steps from the Beach!

9.8 out of 10, Exceptional, (29)
"We stayed at this property weekend of Nov 23rd, 2024. The house is super nice. Very clean. Other than food, the home is stocked with everything you need in the kitchen, bathrooms and bedrooms. Plenty of restaurants, groceries and other shopping nearby. We had an 8 month old and did not feel uncomfortable at all. Would rent again and would recommend this property to anyone. "
Charming Coastal Retreat Steps from the Beach!
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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Other property types in Middlefield

Amazing Lakefront Property
Dining

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property
New Haven Village Suites
Front of property

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (1981)
"It was good"
The price is AED 307
AED 354 total
includes taxes & fees
26 Dec - 27 Dec
New Haven Village Suites
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Miscellaneous

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
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.