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

Guilford Vacation Rentals

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Our top choices for Guilford vacation rentals

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 ¥49,796
¥103,471 total
includes taxes & fees
Sep 14 - Sep 15
Historic New England home ,Reunions Beach pass

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, (186 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is ¥22,501
¥39,314 total
includes taxes & fees
Oct 5 - Oct 6
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

3. 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 ¥28,098
¥51,396 total
includes taxes & fees
Sep 8 - Sep 9
The gardners Cottage 1 mile from long Island Sound - pet friendly

4. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"Was very happy with how wonderfully beautiful the place was. The host was excellent and answered any questions I had promptly. I really appreciate how nice he was."
United States
Elizabeth C.
The price is ¥31,064
¥98,554 total
includes taxes & fees
Sep 9 - Sep 10
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

5. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
10.0 out of 10, Exceptional, (31 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
The price is ¥101,465
¥160,627 total
includes taxes & fees
Sep 6 - Sep 7
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

6. Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (13 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
The price is ¥45,659
¥97,481 total
includes taxes & fees
Sep 7 - Sep 8
Clear LI Sound waterview, Wedding pics, Yale&Beach

7. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ¥19,669
¥36,957 total
includes taxes & fees
Sep 28 - Sep 29
1-bedroom cottage with Grove Beach 🏖️ access.

8. Steps to Beach • Hot Tub • Game Room • Water Views

Steps to Beach • Hot Tub • Game Room • Water Views
Branford
The price is ¥124,880
¥201,681 total
includes taxes & fees
Sep 13 - Sep 14
Steps to Beach • Hot Tub • Game Room • Water Views

9. 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 ¥28,572
¥77,103 total
includes taxes & fees
Sep 9 - Sep 10
Adorable Cottage, 5 min walk to water & town

10. Coastal Landing Stay

Coastal Landing Stay
East Shore
The price is ¥31,844
¥78,975 total
includes taxes & fees
Sep 6 - Sep 7
Coastal Landing Stay

11. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (53 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is ¥46,811
¥53,481 total
includes taxes & fees
Sep 14 - Sep 15
North Fork Resort

12. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (290 reviews)
"Great place!"
United States
Christine
The price is ¥45,608
¥66,037 total
includes taxes & fees
Sep 27 - Sep 28
Cliffside Resort Condominiums

13. 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.
Spacious 2 Bedroom apartment close to Yale Bowl

14. 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 ¥18,420
¥45,535 total
includes taxes & fees
Sep 6 - Sep 7
Once the old Schools house now a newly furnished Apartment

15. Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is ¥26,537
¥50,186 total
includes taxes & fees
Sep 29 - Sep 30
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

16. Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
East Shore
8.8 out of 10, Excellent, (5 reviews)
"Fantastic place, amazing hosts, 100% recommend! "
United States
Zach P.
The price is ¥45,280
¥117,361 total
includes taxes & fees
Sep 8 - Sep 9
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

17. Relaxing 3-bedroom apartment in New Haven

Relaxing 3-bedroom apartment in New Haven
New Haven
9.6 out of 10, Exceptional, (4 reviews)
"Appreciated clean and private bedrooms with own tv in each room."
United States
Bryce B.
The price is ¥26,131
¥57,680 total
includes taxes & fees
Sep 7 - Sep 8
Relaxing 3-bedroom apartment in New Haven

18. 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 ¥16,859
¥38,167 total
includes taxes & fees
Sep 8 - Sep 9
Bright Downtown Studio near Yale & East Rock!

19. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (12 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is ¥33,752
¥73,426 total
includes taxes & fees
Sep 9 - Sep 10
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

20. 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 ¥23,415
¥55,142 total
includes taxes & fees
Sep 7 - Sep 8
Angelica’s safe haven @ west haven
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

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:

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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 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.