Photo by Bibek Magar

Guilford Holiday Rentals

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Holiday Rentals 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, (2024)
"Good stay. "
New Haven Village Suites

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
The price is HK$1,117
HK$1,613 total
includes taxes & fees
30 Apr - 1 May
Cliffside Resort Condominiums

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (7)
"We had a GREAT time here!! Just beautiful scenery all around. The cabin was well equipped with everything we needed essentially. I was quite impressed with how comfortable we actually were. There was a temporary power outage but it didn’t last long and management not only delivered more wood to us but also gave it to us for free as we wanted to spend our time outdoors during the outage. Im super happy to have had this experience and would absolutely be doing it again!! Thank you Postcard...
The price is HK$1,047
HK$1,204 total
includes taxes & fees
29 Apr - 30 Apr
Postcard Cabins Machimoodus

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (128)
"having previously rented VRBO properties in Palm Springs, West Palm Beach & Ft. Lauderdale I can confirm this property is exceptional. The studio has 1st tier amenities, waterfront location & in addition the hosts provided most welcoming foods and snacks, an overall wonderful experienceJimBrooklyn, NY"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (42)
"Love their kitchen. Room is clean and comfortable. The staff is helpful. Will turn. "
Luxury Furnished Apartments by Hyatus Downtown at Yale

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Beautiful location, lovely neighbors. House is dated as seen in photos. "
The price is HK$1,551
HK$3,493 total
includes taxes & fees
15 Apr - 16 Apr
adorable ranch in beach community

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

9.8 out of 10, Exceptional, (127)
"We loved our stay!"
The price is HK$2,714
HK$5,232 total
includes taxes & fees
15 Apr - 16 Apr
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

North Fork 7 Bedroom Farmhouse Escape

3.0 star property
9.4 out of 10, Exceptional, (3)
"We were in town for a wedding with small children in tow- the house was perfectly located for us to get to wedding events in under 10 minutes but do be aware that it’s on a busy road. The house is set back so there wasn’t too much traffic noise, especially with the window AC units going. You could walk to the beach, but be aware that it’s down the busy road as someone else mentioned. It wasn’t luxurious, but everything was clean and comfortable. I appreciated that towels and linens were provided...
North Fork 7 Bedroom Farmhouse Escape

COZY Maple Tree Cabin - Situated on 6 private acres - Get Away and RELAX 😎

10.0 out of 10, Exceptional, (28)
"It is certainly a cabin in the quiet woods which you would normally find in northern Vermont. We loved everything about it. My Three Sons grew up tent camping in the Yale Forest and this was that, only with a log cabin replacing Eureka tents! We loved sitting around the massive firepit and feeding the flames with plenty of seasoned, dry hardwood, cooking several meals on the coals with pie irons and steak prongs. Just loved it. "
The price is HK$2,908
HK$5,562 total
includes taxes & fees
15 Apr - 16 Apr
COZY Maple Tree Cabin - Situated on 6 private acres - Get Away and RELAX 😎

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (70)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.

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

10.0 out of 10, Exceptional, (55)
"Lovely, spacious and clean. We spent our Christmas holiday together with our family and the house was spacious and spotless. We had 5 adults with 2 small children in house. We hosted Christmas dinner for us and local family. Great space. Would love to rent in summer months to utilize outdoor space"
Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (13)
"Great. Would prefer to anyone"
Luxury Apartments by Hyatus at Pierpont

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

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
The price is HK$2,326
HK$5,009 total
includes taxes & fees
18 Apr - 19 Apr
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

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

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is HK$872
HK$1,846 total
includes taxes & fees
15 Apr - 16 Apr
The Mast at Soundview · Beach+Ocean+Sunrise

Shoreline Oasis

The price is HK$1,388
HK$2,021 total
includes taxes & fees
15 Apr - 16 Apr
Shoreline Oasis

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

9.6 out of 10, Exceptional, (33)
"Lovely little cottage in a pretty, quiet neighborhood. Once you find it down the little lane, it's a great location to be in. Not far from town and close to the water, we really enjoyed relaxing at the house and in the backyard. Highly recommend."
The price is HK$2,353
HK$4,532 total
includes taxes & fees
7 May - 8 May
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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 types of properties in Guilford you may be interested in

New Haven Hotel

3.5 star property
8.8 out of 10, Excellent, (1497)
"Flight got cancelled and glad I booked this hotel. The rate was good. The hotel was downtown and walking distance to restaurants and Yale University. "
The price is HK$916
HK$1,054 total
includes taxes & fees
27 Apr - 28 Apr
New Haven Hotel

Holiday Inn Express Southington by IHG

2.5 star property
8.8 out of 10, Excellent, (1013)
"Comfy beds and responsive and accommodating staff!"
The price is HK$663
HK$762 total
includes taxes & fees
20 Apr - 21 Apr
Holiday Inn Express Southington by IHG

Water's Edge Resort & Spa

3.5 star property
8.8 out of 10, Excellent, (1003)
"Staff is always very receptive and cordial!"
The price is HK$1,543
HK$1,908 total
includes taxes & fees
15 Apr - 16 Apr
Water's Edge Resort & Spa
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.

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?

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!: This highly rated holiday home rental in Guilford is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Guilford?

Expedia has 27 holiday rentals for your stay in Guilford.

What’s there to see and do in Guilford?

Cultural attractions include Hyland House Museum and Henry Whitfield State Museum, whereas Chaffinch Island State Park is one spot to enjoy nature. Other places in town to visit include Bishops Orchard and Winery and Stony Creek - Thimble Islands Historic District.

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.