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Compare 585 Vacation Homes in Guilford with updated reviews, rates, and availability.

Waterfront House with picture-perfect views from all 3 levels.

9.8 out of 10, Exceptional, (84)
"We stayed in Saybrook for 3 day weekend for a wedding. Our home had spectacular views of the water. The house was roomy for all of us with 3 bedrooms, plenty of kitchen for several adults and bar and eating area.Our hosts provided helpful information through VRBO and written in the home. We would love to come back in the Summer."
Waterfront House with picture-perfect views from all 3 levels.

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (24)
"Had a wonderful stay. The house was large enough to allow us all to have our own rooms. Location was perfect and within walking distance of everything. "
Large Charming Historic House close to Beaches

Cozy Westbrook Vacation Rental - Walk to Beach!

9.8 out of 10, Exceptional, (17)
"Stayed at this house for a weekend after Christmas. It was great! Perfect location and easy to get everywhere! Would love to stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (57)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Waterfront Beach House

9.6 out of 10, Exceptional, (42)
"The property is nicely located on the water and convenient to many attractions. "
Waterfront Beach House

Luxe Lake House in Connecticut

10.0 out of 10, Exceptional, (2)
"Couldn’t have asked for a better weekend! Thank you so much Shawn! "
The price is AED 1,288
AED 3,322 total
includes taxes & fees
6 May - 7 May
Luxe Lake House in Connecticut

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

9.0 out of 10, Wonderful, (89)
"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! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

10.0 out of 10, Exceptional, (55)
"We really enjoyed our stay at the property. The home was very clean, the beds were comfortable, and the location was convenient for all of our weekend activities."
Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

Magic Place

The price is AED 1,653
AED 3,357 total
includes taxes & fees
6 May - 7 May
Magic Place

Waterfront Lakehouse in Clinton, CT with Hot Tub!

7.0 out of 10, Good, (2)
"My family and I absolutely loved our stay at this home! It was the perfect retreat for us, and we thoroughly enjoyed the hot tub and the breathtaking sunset views, especially while cooking in the beautifully designed kitchen. The kitchen was fully equipped, making it easy to prepare an amazing family dinner. The town of Clinton was absolutely charming, with the friendliest people, and we fell in love with Hammonasset Beach—it’s a must-visit! We’ll definitely be returning in the summer. The...
Waterfront Lakehouse in Clinton, CT with Hot Tub!

North Fork Family and Friends Getaway. Great Location

10.0 out of 10, Exceptional, (9)
"We had a great stay! The house had everything we needed and was in a wonderful location to explore the North Fork. Barbara was incredibly gracious - very responsive and helpful. We hope to make a return visit!"
North Fork Family and Friends Getaway. Great Location

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (12)
"Enjoyable stay, nice property and great views. The home is aged, but the location is amazing! We had a nice weekend excursion to enjoy New England in October. "
Grammy's Lake House w/ Private Waterfront Access

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (42)
"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

10.0 out of 10, Exceptional, (7)
"It was a great house to host our family for Thanksgiving dinner! "
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

10.0 out of 10, Exceptional, (11)
"This pet friendly home is located in a great residential neighborhood close to Yale campus and the bowl. Very clean and comfortable. Great fenced yard for pets and kids."
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (6)
"Our experience with this facility, from online service to exiting the residence, was the most pleasurable experience, for staying in accommodations when traveling!!The owner was a complete gentleman and it was absolutely wonderful experience to meet and talk with him."
Family Stays: Middletown, CT

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (70)
"My husband and I stayed in this lovely home for a long weekend while attending the Soundside music festival. It was perfect for what we were looking for; comfortable beds, equipped kitchen and nice location. We had the entire private beach to ourselves. The owners were also quick to respond to all questions. "
Beautiful 4BR Beach House with Private Beach Access.

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (117)
"Had a quick work trip and wish we stayed longer! "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (27)
"The property was perfect for our beach vacation."
The price is AED 2,241
AED 3,847 total
includes taxes & fees
16 May - 17 May
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

9.4 out of 10, Exceptional, (3)
"We stayed for a week and the house was perfect. Comfortable, so clean, very well stocked, really nice decor and a fantastic location. Host was very helpful and responsive. Highly recommend and we will definitely be back. "
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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 Guilford

🌾Brand New Tiny Home! Downtown & Beachy☀️

10.0 out of 10, Exceptional, (4)
"Just went for a few days, and decided to stay an extra night! Hostess was wonderful as well, and very helpful! Will definitely be going back!"
🌾Brand New Tiny Home! Downtown & Beachy☀️

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

10.0 out of 10, Exceptional, (26)
"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!

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2027)
"Okay place to stay "
New Haven Village Suites
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.