A coastal landscape with a lighthouse, beach, rocky outcrops, and a distant city skyline.

Guilford Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Guilford holiday rentals

A covered patio with a glass table, white metal chairs, a green sofa, and a white metal bench.

1. Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.2 out of 10, Wonderful, (90 reviews)
"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 NZ$1,121
includes taxes & fees
22 Sept - 23 Sept
Historic New England home ,Reunions Beach pass
A cabin with a large window, surrounded by trees.

2. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (189 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is NZ$340
includes taxes & fees
21 Sept - 22 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

3. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (56 reviews)
"We enjoyed our stay"
United States
JM B.
The price is NZ$393
includes taxes & fees
6 Oct - 7 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

4. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is NZ$543
includes taxes & fees
7 Oct - 8 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

5. One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
The price is NZ$314
includes taxes & fees
28 Sept - 29 Sept
One bedroom in United States of America, New Haven

6. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is NZ$498
includes taxes & fees
12 Oct - 13 Oct
All New 1BR with tons of Charm
A row of brownstone buildings with a central staircase leading to the second floor.

7. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.2 out of 10, Wonderful, (16 reviews)
"Pretty close to Yale campus"
United States
Dongjian
The price is NZ$416
includes taxes & fees
4 Oct - 5 Oct
Bright Downtown Studio near Yale & East Rock!
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

8. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is NZ$397
includes taxes & fees
23 Sept - 24 Sept
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
A modern living room with a large mirror, a wooden accent wall, a grey sofa, and a large window with white curtains.

9. The Elm - Retreat Near Yale, Parking, Gym, DTWN, Wooster Sq & Union Stn.

The Elm - Retreat Near Yale, Parking, Gym, DTWN, Wooster Sq & Union Stn.
Downtown New Haven
10.0 out of 10, Exceptional, (5 reviews)
"Great little downtown apartment! Small - good for up to two people. Nicely appointed and decorated, great sectional sofa, big TVs where we wanted them. Host was kind and helpful and accommodating. Location is pretty much across State St from the State Street RR Station, a block and a half from the Green, and near everything. Orange Street (half a block away) has a ton of bars and restaurants. We enjoyed our stay!"
United States
George Z.
The Elm - Retreat Near Yale, Parking, Gym, DTWN, Wooster Sq & Union Stn.
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

10. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is NZ$501
includes taxes & fees
28 Sept - 29 Sept
Once the old Schools house now a newly furnished Apartment
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

11. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is NZ$821
includes taxes & fees
20 Sept - 21 Sept
Adorable Cottage, 5 min walk to water & town
A modern building with reflective glass facades, a central atrium, and a landscaped area with trees and pathways.

12. GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds

GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
East Rock
10.0 out of 10, Exceptional, (4 reviews)
"Perfect for families."
United States
Frances
The price is NZ$832
includes taxes & fees
22 Sept - 23 Sept
GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a white table and chairs.

13. Stylish Wooster Square Home Walk to Yale

Stylish Wooster Square Home Walk to Yale
Downtown New Haven
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful apartment in the Wooster neighborhood. New, modern, comfortable apartment within walking distance to great restaurants. Nicely appointed with easy check-in and parking for one car. Was perfect for two couples visiting their Yale students for the weekend!"
United States
Lydia P.
The price is NZ$507
includes taxes & fees
21 Sept - 22 Sept
Stylish Wooster Square Home Walk to Yale
A cozy living room with a grey sofa, a coffee table with books and a vase of flowers, and bookshelves filled with books and decorative items.

14. Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very good, (9 reviews)
"We had a good time. Did some relaxing, a little beachtime and ate some good food."
United States
Erin S.
The price is NZ$429
includes taxes & fees
28 Sept - 29 Sept
Spacious Bohemian Nook
A conference room with a long wooden table, black chairs, a blue runner, a jar of candies, a small box, and a framed artwork on the wall.

15. Stocked home close to Yale, in Heart of New Haven

Stocked home close to Yale, in Heart of New Haven
Mill River
9.0 out of 10, Wonderful, (28 reviews)
"Great value very close to university. "
United States
Lawrence
The price is NZ$393
includes taxes & fees
21 Sept - 22 Sept
Stocked home close to Yale, in Heart of New Haven
A living room with a dark grey sofa, two wooden chairs, a small table with a tray, and a large window with a view of the sea.

16. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (95 reviews)
"Great cottage on the Sound!"
United States
David S.
The price is NZ$1,754
includes taxes & fees
28 Sept - 29 Sept
Direct waterfront renovated cottage.
A neatly made bed with a checkered blanket, white pillows, and a framed picture on the wall.

17. Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.2 out of 10, Wonderful, (15 reviews)
"We had a very nice stay here! The hosts were lovely and very communicative, and they were able to help us with any problems we had very quickly."
United States
Luke
The price is NZ$326
includes taxes & fees
23 Sept - 24 Sept
Yale Casa Verde Studio
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

18. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (36 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is NZ$461
includes taxes & fees
29 Sept - 30 Sept
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A house with a front porch, a garage, and a well-maintained lawn.

19. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (7 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is NZ$571
includes taxes & fees
18 Sept - 19 Sept
Angelica’s safe haven @ west haven
A dining area with a long table, four chairs, a chandelier, and a painting on the wall.

20. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (79 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
The price is NZ$366
includes taxes & fees
21 Sept - 22 Sept
Spacious 2 Bedroom apartment close to Yale Bowl
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

Zey Hotel

Zey Hotel

10/10 Excellent
"Great time, great stay, great staff! Will definitely be coming back!"
Amanda 2-night trip
Posted 12 hours ago
Zey Hotel

Find out more about Guilford

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Guilford holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Guilford. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Guilford. Seeing all the best attractions is bound to make you fall in love with Guilford. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Guilford short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Guilford?

Yes, there are holiday rentals in Guilford close to Guilford Art Center, 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?

TREETOPS house! AUG openings! A Reunion/Retreat estate! Seasonal POOL! Sleeps 12: 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 29 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 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.