Photo by Bibek Magar

Guilford Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Guilford vacation rentals

Fridge, microwave, oven, stovetop
Historic New England home ,Reunions Beach pass

Vacation Home in Guilford

Historic New England home ,Reunions Beach pass
9.2 out of 10, Wonderful, (90)
"This is a great location, walking distance to the green and other sites. It also worked well for our girls trip of 4 women."
United States
Liz H.
The price is ￥42,274
￥84,078 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Historic New England home ,Reunions Beach pass
Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Cabin in East Haddam

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (95)
"My wife loved it…she has a rough week with work and just life in general, so I wanted to do something nice for her and surprised her with a stay here…she was really happy and loved everything about it…can’t wait to do this again 😊"
United States
Keven
The price is ￥18,581
￥28,551 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is ￥11,873
￥30,190 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (36)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is ￥11,555
￥27,043 total
includes taxes & fees
Dec 28 - Dec 29
1-bedroom cottage with Grove Beach 🏖️ access.
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

Vacation Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (5)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
The price is ￥13,520
￥63,045 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Rogers Lake House (87) · CT College+Beach+USCGA
Private kitchen
Westville Stay • 2BR • Near Yale • Free Parking

Apartment in West New Haven

Westville Stay • 2BR • Near Yale • Free Parking
10.0 out of 10, Exceptional, (3)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is ￥13,308
￥37,420 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Westville Stay • 2BR • Near Yale • Free Parking
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Vacation Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥18,006
￥45,132 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Once the old Schools house now a newly furnished Apartment
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is ￥13,387
￥25,729 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
1 bedroom, desk, iron/ironing board, WiFi
One bedroom apartment in United States of America, New Haven

Apartment in Dwight

One bedroom apartment in United States of America, New Haven
9.4 out of 10, Exceptional, (3)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is ￥14,833
￥32,165 total
includes taxes & fees
Jan 27 - Jan 28, 2026
One bedroom apartment in United States of America, New Haven
Fridge, microwave, oven, stovetop
#26 Beautifully Renovated 2 BR Home

Vacation Home in Plainville

#26 Beautifully Renovated 2 BR Home
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is ￥18,261
￥36,656 total
includes taxes & fees
Jan 5 - Jan 6, 2026
#26 Beautifully Renovated 2 BR Home
Interior
Cozy Guest Suite in Historic Home

Vacation Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is ￥23,110
￥33,622 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cozy Guest Suite in Historic Home
Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Apartment in East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
9.6 out of 10, Exceptional, (10)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
The price is ￥15,458
￥41,985 total
includes taxes & fees
Dec 28 - Dec 29
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Vacation Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is ￥16,596
￥47,190 total
includes taxes & fees
Dec 28 - Dec 29
Private Apartment in Berlin
Exterior
Charming Studio| Near Yale| Downtown New Haven

Apartment in Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (12)
"Convenient location. Just off Rte 91. Easy street parking. The studio is as pictured - exposed brick walls, high ceilings. Everything you need for a short stay. "
United States
Lois G.
The price is ￥9,837
￥27,637 total
includes taxes & fees
Dec 29 - Dec 30
Charming Studio| Near Yale| Downtown New Haven
Exterior
Newly Remodeled with deck. Close to town center

Apartment in Wallingford

Newly Remodeled with deck. Close to town center
10.0 out of 10, Exceptional, (2)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is ￥17,956
￥44,227 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Newly Remodeled with deck. Close to town center
Fridge, microwave, oven, stovetop
New Railside Residents

Apartment in Wallingford Center

New Railside Residents
10.0 out of 10, Exceptional, (1)
"This apartment was the perfect base for visiting family in Wallingford. It had everything we needed, was very clean, and super convenient to downtown cafes and restaurants. The train is a bit loud but to be expected! Will definitely stay again. "
United States
Kelsey S.
New Railside Residents
Interior
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Apartment in Haddam

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
10.0 out of 10, Exceptional, (27)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is ￥19,571
￥40,082 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Fridge, microwave, oven, stovetop
All New 1BR with tons of Charm

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (7)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is ￥17,956
￥45,007 total
includes taxes & fees
Jan 11 - Jan 12, 2026
All New 1BR with tons of Charm
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Vacation Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥21,356
￥78,615 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Beachside Bliss w/ Game Room, Gym & Golf Green
Fridge, microwave, oven, stovetop
LONG-TERM Winter by the Ocean and Ski Resort 30 mins away

Vacation Home in Clinton

LONG-TERM Winter by the Ocean and Ski Resort 30 mins away
2.0 star property
10.0 out of 10, Exceptional, (3)
"Vincent was amazing to work with! We decided to change the dates and he was very patient and helpful while we got it updated with VRBO. The home is in a peaceful neighborhood with beautiful trees and active squirrels (my daughter’s favorite part). The location was convenient for our needs. We all enjoyed the game tables and the convenience of the washer and dryer. We even tried out the projector one night to watch a couple of episodes of Gilmore Girls – so fun! Vincent checked in once we arrived...
United States
Erin S.
The price is ￥22,405
￥83,893 total
includes taxes & fees
Jan 4 - Jan 5, 2026
LONG-TERM Winter by the Ocean and Ski Resort 30 mins away
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Guilford Hotel Reviews

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

10/10 Excellent
"Great stay overall. Wish it was easier to walk to good restaurants. Had to drive to good food."
James 1-night trip
Posted 21 hours ago
Cambria Hotel New Haven University Area

Find out more about Guilford

Search for holiday rentals in Guilford on Expedia! You can easily find your home rentals, villas, holiday apartments in Guilford using one of the methods below:

  • View our selection of featured holiday rentals in Guilford
  • Use the map to find apartments and other holiday homes in the Guilford neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Guilford while they last

Look no further and take a look at our great range of rental properties in Guilford!

Frequently asked questions

Can I find a vacation rental in Guilford?

Yes, there are vacation rentals close to well known local attractions in Guilford, or you can select a secluded option if you'd like a relaxing place to stay. Our travelers say Guilford has a good selection of restaurants. Make sure you have time to check out the sightseeing tours and wineries during your trip.

What are some of the best vacation rentals in Guilford?

Private Apartment in Berlin: This vacation home near Guilford is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Guilford?

Expedia has 27 vacation rentals for your stay in Guilford.

What’s there to see and do in Guilford?

Cultural attractions include Guilford Art Center and Hyland House Museum, whereas Guilford Town Green and Chaffinch Island State Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Stony Creek - Thimble Islands Historic District and Bishops Orchard and Winery.

What’s a vacation rental in Guilford like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Guilford. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family getaway.