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

Guilford Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Guilford vacation 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.
$534 nightly
The price is $609
Sep 29 - Sep 30
Total with taxes and fees
Historic New England home ,Reunions Beach pass
A cabin with a dining table set for two, a bicycle, and a small porch area.

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, (194 reviews)
"ABSOLUTELY BEAUTIFUL AND SERENE STAY . WE REALLY ENJOYED OUR STAY !"
United States
Melissa
$175 nightly
The price is $201
Oct 28 - Oct 29
Total with taxes and fees
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, (60 reviews)
"We enjoyed our stay"
United States
JM B.
$199 nightly
The price is $226
Oct 26 - Oct 27
Total with taxes and fees
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)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$253 nightly
The price is $287
Oct 7 - Oct 8
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
A living room with a dark sofa, a coffee table with items, a window with a view of a house, and a bookshelf.

5. Cozy 1-bedroom apartment in peaceful Branford with AC and gym access

Cozy 1-bedroom apartment in peaceful Branford with AC and gym access
Branford
$180 nightly
The price is $204
Sep 30 - Oct 1
Total with taxes and fees
Cozy 1-bedroom apartment in peaceful Branford with AC and gym access
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

6. 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.
$159 nightly
The price is $180
Oct 27 - Oct 28
Total with taxes and fees
One bedroom in United States of America, New Haven
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
$210 nightly
The price is $239
Sep 29 - Sep 30
Total with taxes and fees
Bright Downtown Studio near Yale & East Rock!
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

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

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$263 nightly
The price is $281
Sep 29 - Sep 30
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

9. 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.
$194 nightly
The price is $210
Sep 29 - Sep 30
Total with taxes and fees
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
A compact kitchen with grey cabinets, a built-in microwave, a coffee machine, and a sink with a modern faucet.

10. All New Fully Furnished Cozy Studio

All New Fully Furnished Cozy Studio
Wallingford Center
9.8 out of 10, Exceptional, (9 reviews)
"Clean and well designed apartment in a great location. Book here if you are interested as you won't have any regrets. Enjoy! "
United States
Rick C.
$263 nightly
The price is $281
Oct 4 - Oct 5
Total with taxes and fees
All New Fully Furnished Cozy Studio
A modern living room with a flat-screen TV, a sofa, a blue chair, and a large potted plant.

11. Relaxing 3-bedroom apartment in New Haven

Relaxing 3-bedroom apartment in New Haven
New Haven
9.6 out of 10, Exceptional, (5 reviews)
"To be honest with you overall the stay was decent. The host was very accommodating for us as we wanted to check in early due to our flight, arriving in the morning. When we had issues with the linens needing to be changed I called our host she was super responsive and immediately had housekeeping there to rectify our issues. The only thing I could say about the property is the furniture, especially in the living area needs to be updated. Also, the property could use some TLC when it comes to the...
United States
S F.
$321 nightly
The price is $366
Sep 29 - Sep 30
Total with taxes and fees
Relaxing 3-bedroom apartment in New Haven
A marina with multiple docks and boats, surrounded by residential buildings and greenery.

12. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.8 out of 10, Exceptional, (16 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
$261 nightly
The price is $284
Sep 29 - Sep 30
Total with taxes and fees
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Exterior

13. Prime Yale Studio Steps to Sallys Apizza

Prime Yale Studio Steps to Sallys Apizza
Downtown New Haven
10.0 out of 10, Exceptional, (1 review)
"Great stay - and it is close to Sally's! We had a nice visit and all was as represented for the property."
United States
Milton W.
$177 nightly
The price is $201
Sep 29 - Sep 30
Total with taxes and fees
Prime Yale Studio Steps to Sallys Apizza
A dining area with a long table, four chairs, a chandelier, and a painting on the wall.

14. 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.
$182 nightly
The price is $206
Sep 29 - Sep 30
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
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.

15. 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, (37 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.
$220 nightly
The price is $250
Oct 19 - Oct 20
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

16. 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.
$393 nightly
The price is $448
Oct 15 - Oct 16
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
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.

17. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (96 reviews)
"Unbeatable views and professional hosts."
United States
Russell A.
Direct waterfront renovated cottage.
A modern living room with a large mirror, a wooden accent wall, a grey sofa, and a large window with white curtains.

18. 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, (6 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.
$279 nightly
The price is $318
Sep 29 - Sep 30
Total with taxes and fees
The Elm - Retreat Near Yale, Parking, Gym, DTWN, Wooster Sq & Union Stn.
A modern apartment with a green sofa, a wooden dining table, and a kitchen in the background.

19. Modern Westville Home near Yale and Hospitals

Modern Westville Home near Yale and Hospitals
West New Haven
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and comfortable space. Excellent location and parking was a plus. We have stayed here twice and would definitely recommend to friends or family. "
United States
Thomas B.
$209 nightly
The price is $238
Sep 29 - Sep 30
Total with taxes and fees
Modern Westville Home near Yale and Hospitals
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.

20. 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.
$218 nightly
The price is $247
Sep 29 - Sep 30
Total with taxes and fees
Spacious Bohemian Nook
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

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Always a terrific stay"
Louis 1-night trip
Posted 1 hour ago
New Haven Hotel

Find out more about Guilford

Everything you need to know about Guilford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Guilford vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Guilford vacation 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 low season months. For more hustle and bustle, you may prefer to visit Guilford in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $201 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Guilford rentals

At Expedia, we put the best Guilford vacation 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 vacation.

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.

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Frequently asked questions

Can I find a vacation rental in Guilford?

Yes, there are vacation rentals in Guilford close to Guilford Art Center, or you can select a more 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?

TREETOPS house! AUG openings! A Reunion/Retreat estate! Seasonal POOL! Sleeps 12: This highly rated vacation home rental in Guilford is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals are there in Guilford?

Expedia has 30 vacation 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 Sachem Head Harbor 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.