Guilford Holiday Rentals

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Our top choices for Guilford holiday rentals

9.2 out of 10, Wonderful, (90)
"The location of this place is best!"
United States
Dr. Maureen C.
The price is NZ$705
includes taxes & fees
21 Dec - 22 Dec
Historic New England home ,Reunions Beach pass
9.6 out of 10, Exceptional, (88)
"Clean and good service."
United States
Simge
The price is NZ$314
includes taxes & fees
14 Dec - 15 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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 NZ$332
includes taxes & fees
6 Jan - 7 Jan 2026
The Stern at Soundview · Beach+Ocean+Sunrise
10.0 out of 10, Exceptional, (4)
"Communication was excellent. "
United States
Katy C.
The price is NZ$692
includes taxes & fees
8 Jan - 9 Jan 2026
Rogers Lake House (87) · CT College+Beach+USCGA
9.8 out of 10, Exceptional, (21)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
The price is NZ$504
includes taxes & fees
14 Dec - 15 Dec
#24 *Serenity* A Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (6)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is NZ$576
includes taxes & fees
13 Dec - 14 Dec
Angelica’s safe haven @ west haven
10.0 out of 10, Exceptional, (2)
"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.
Westville Stay • 2BR • Near Yale • Free Parking
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 NZ$882
includes taxes & fees
14 Dec - 15 Dec
LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins

Holiday Home in Middletown

Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (18)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
United States
Cari M.
The price is NZ$371
includes taxes & fees
15 Dec - 16 Dec
Family Stays: Middletown, CT
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 NZ$888
includes taxes & fees
16 Dec - 17 Dec
Beachside Bliss w/ Game Room, Gym & Golf Green

Apartment in Clinton

Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is NZ$445
includes taxes & fees
12 Dec - 13 Dec
Shoreline Oasis
10.0 out of 10, Exceptional, (2)
"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 NZ$352
includes taxes & fees
18 Dec - 19 Dec
One bedroom apartment in United States of America, New Haven
9.2 out of 10, Wonderful, (36)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
The price is NZ$309
includes taxes & fees
15 Dec - 16 Dec
1-bedroom cottage with Grove Beach 🏖️ access.

Holiday 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 NZ$403
includes taxes & fees
15 Dec - 16 Dec
#26 Beautifully Renovated 2 BR Home
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 NZ$426
includes taxes & fees
17 Dec - 18 Dec
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
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 NZ$281
includes taxes & fees
22 Dec - 23 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.8 out of 10, Exceptional, (8)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
#23 *COMFORT & LUXURY* 3 BR/2 BA House
10.0 out of 10, Exceptional, (27)
"Overall wonderful experience, would highly recommend."
United States
Steven R.
The price is NZ$444
includes taxes & fees
10 Jan - 11 Jan 2026
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Holiday Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is NZ$543
includes taxes & fees
14 Dec - 15 Dec
Private Apartment in Berlin
10.0 out of 10, Exceptional, (4)
"Such a cute place, loved all the nautical touches. Great space for a weekend getaway, pretty well-stocked kitchen, clean & cozy. Really appreciated the outdoor space & amenities too! And Michael the host is very responsive & helpful! "
United States
Amal A.
The price is NZ$257
includes taxes & fees
12 Dec - 13 Dec
Cozy East Haven Home • Near Beach & Yale
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 Guilford Hotel Reviews

Find out more about Guilford

Everything you need to know about Guilford holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Guilford holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Guilford holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Guilford holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Guilford. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Guilford holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Guilford holiday rentals we have selected for you start as low as NZ$222 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Guilford rentals

At Expedia, we put the best Guilford holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Guilford rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Guilford holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Guilford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Guilford?

Yes, there are holiday rentals close to the most popular sights in Guilford, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Guilford has to offer?

Private Apartment in Berlin: This holiday home rental outside of 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 holiday rentals are there in Guilford?

Expedia has 28 holiday 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 holiday rental in Guilford like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Guilford. Holiday rentals provide amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.