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Compare 484 Vacation Homes in Guilford with updated reviews, rates, and availability.

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (23)
"This was the BEST decision for our family. The house was very cozy, old charm feel with some modern updates. The downstairs bathroom had a Spa vibe. We loved the 6 bedrooms & spacious kitchen & dining room. Loved how close it was to food & entertainment. The walk to the beach was only 10 minutes & very safe. We are use to blinds and/or shades, so just having light curtains for the windows was"
Large Charming Historic House close to Beaches

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

9.6 out of 10, Exceptional, (78)
"Hosts were great with easy and quick communication! House was very clean and everything is clearly labeled. "
Waterfront House with picture-perfect views from all 3 levels.

Luxe Lake House in Connecticut

10.0 out of 10, Exceptional, (2)
"The house easily accommodated my friends and family for a weekend of relaxation. The place is very spacious with all modern amenities. We especially loved waking up to the gorgeous view of the lake in the back. The views were breathtaking. Would definitely consider going back. "
The price is AED 1,230
AED 3,247 total
includes taxes & fees
18 Mar - 19 Mar
Luxe Lake House in Connecticut

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

9.0 out of 10, Wonderful, (87)
"Everything was just fine - nothing spectacular but good enough for a short stay. Extremely safe feeling location"
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!

9.6 out of 10, Exceptional, (45)
"We stayed for the weekend to attend a wedding nearby and it was the perfect little cottage for a beach getaway! The place was very clean and so beautifully decorated, and the location can't be beat!"
Insta-worthy Couples Retreat: Perfect for romantic getaway!

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!

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

9.8 out of 10, Exceptional, (127)
"We loved our stay!"
The price is AED 1,058
AED 2,187 total
includes taxes & fees
11 Mar - 12 Mar
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (59)
"Our family ranged in ages from 13 to 96. We were 12 people for a couple days and then 10. We all had a marvelous time and my mom just can’t stop talking about how beautiful the view and the antique furniture was. It was difficult for that many people only having two bathrooms, but we made it work. We did run out of hot water so we learned to scatter showers when possible. The view is amazing and the location was wonderful for us. I can’t say enough, how accommodating our hostess was. We told her...
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

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

10.0 out of 10, Exceptional, (116)
"The Arts and Crafts home was more beautiful than the pictures reflected! We loved all of the details in the woodwork, hidden little corners, tons of space to spread out and wonderful places to gather together. Having recently sold our "family home" we were thrilled to find this home in which to have a mini- family reunion. The kitchen was incredibly well-stocked- from serving platters to garlic powder to paper towels...We had everything we needed. The gas fireplace created a beautiful focal...
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

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

10.0 out of 10, Exceptional, (56)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025

The SandPiper

9.6 out of 10, Exceptional, (20)
"My friends and I stayed here for a night after a wedding. It was the perfect place to stay after a long day. Host was kind and helpful with anything I needed! "
The SandPiper

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

10.0 out of 10, Exceptional, (13)
"The apartment was on the first floor, we had access to park in the driveway. The apartment was recently renovated, clean and well stocked with everything you need. Walking distance to town. Very spacious and comfortable. would definitely stay again!"
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Historic Essex Home w/ Large Yard Near Downtown!

10.0 out of 10, Exceptional, (45)
"A lovely home in a great area! We will be back!"
Historic Essex Home w/ Large Yard Near Downtown!

North Fork Family and Friends Getaway. Great Location

10.0 out of 10, Exceptional, (9)
"10 of us stayed at this house during LDW and had the most incredible experience. The pictures do not do the house justice- it was even better than we anticipated. Beyond gorgeous, so clean, huge, and the backyard will leave you speechless. We cannot recommend it enough. The only downside was the bedrooms upstairs were warm. Thank you to our amazing hosts!!!! We will be back. "
North Fork Family and Friends Getaway. Great Location

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

10.0 out of 10, Exceptional, (6)
"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, (9)
"Is a great location given minutes from Yale. We were able to make a nice meal to celebrate our son’s success. Nice place!"
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (5)
"Perfect getaway for a group of ladies spending a snowy night catching up away from our spouses and kids. Cozy fireplace, beautiful home, ample space and in a great location. Highly recommend!"
The price is AED 1,836
AED 3,458 total
includes taxes & fees
10 Mar - 11 Mar
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

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

Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF

9.8 out of 10, Exceptional, (115)
"Beautiful house, sitting high and overlooking the Connecticut River. Can't imagine a more beautiful setting. Very large kitchen, great for cooking in with friends. Even has an adjacent helicopter pad (although it's $4k to go from Hartford airport to the house, 1-way!). Had a great time."
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
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

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

10.0 out of 10, Exceptional, (25)
"This house is amazing! Has everything we needed for our stay and very clean. Dan was accessible and very responsive at all times. Highly recommend!"
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, (2011)
"It was a pleasant stay for my 2 days."
The price is AED 324
AED 373 total
includes taxes & fees
13 Mar - 14 Mar
New Haven Village Suites

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (6)
"I loved this escape from reality. This was a very quiet romantic getaway for Valentine’s Day. The place was very clean and had everything we needed from a fully equipped small kitchen to everything outdoors we would need for a campfire and making s’mores. I loved this place and can’t wait to come back for another romantic getaway."
The price is AED 496
AED 570 total
includes taxes & fees
23 Mar - 24 Mar
Postcard Cabins Machimoodus
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.