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, 90, (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 CA $426
CA $900 total
includes taxes & fees
Sep 30 - Oct 1
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, 188, (188 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is CA $187
CA $279 total
includes taxes & fees
Sep 22 - Sep 23
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, 56, (56 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $167
CA $320 total
includes taxes & fees
Oct 6 - Oct 7
1-bedroom cottage with Grove Beach 🏖️ access.

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, 28, (28 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is CA $243
CA $449 total
includes taxes & fees
Oct 7 - Oct 8
The gardners Cottage 1 mile from long Island Sound - pet friendly

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, 2, (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 CA $111
CA $259 total
includes taxes & fees
Sep 27 - Sep 28
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, 11, (11 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is CA $164
CA $402 total
includes taxes & fees
Sep 16 - Sep 17
All New 1BR with tons of Charm

7. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.2 out of 10, 16, (16 reviews)
"Pretty close to Yale campus"
United States
Dongjian
The price is CA $150
CA $323 total
includes taxes & fees
Sep 16 - Sep 17
Bright Downtown Studio near Yale & East Rock!

8. Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, 5, (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 CA $161
CA $314 total
includes taxes & fees
Sep 21 - Sep 22
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

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, 5, (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.

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, 14, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is CA $164
CA $402 total
includes taxes & fees
Sep 16 - Sep 17
Once the old Schools house now a newly furnished Apartment

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

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, 17, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is CA $230
CA $651 total
includes taxes & fees
Sep 16 - Sep 17
Adorable Cottage, 5 min walk to water & town

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, 4, (4 reviews)
"Perfect for families."
United States
Frances
The price is CA $226
CA $548 total
includes taxes & fees
Sep 16 - Sep 17
GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds

13. Stylish Wooster Square Home Walk to Yale

Stylish Wooster Square Home Walk to Yale
Downtown New Haven
9.8 out of 10, 6, (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 CA $150
CA $378 total
includes taxes & fees
Sep 16 - Sep 17
Stylish Wooster Square Home Walk to Yale

14. Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, 9, (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 CA $156
CA $334 total
includes taxes & fees
Sep 16 - Sep 17
Spacious Bohemian Nook

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, 28, (28 reviews)
"Great value very close to university. "
United States
Lawrence
The price is CA $169
CA $292 total
includes taxes & fees
Sep 16 - Sep 17
Stocked home close to Yale, in Heart of New Haven

16. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, 95, (95 reviews)
"Great cottage on the Sound!"
United States
David S.
The price is CA $876
CA $1,366 total
includes taxes & fees
Sep 28 - Sep 29
Direct waterfront renovated cottage.

17. Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.2 out of 10, 15, (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 CA $111
CA $247 total
includes taxes & fees
Sep 16 - Sep 17
Yale Casa Verde Studio

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, 36, (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 CA $186
CA $372 total
includes taxes & fees
Sep 22 - Sep 23
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

19. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, 7, (7 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is CA $208
CA $466 total
includes taxes & fees
Sep 16 - Sep 17
Angelica’s safe haven @ west haven

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, 79, (79 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
The price is CA $173
CA $312 total
includes taxes & fees
Sep 22 - Sep 23
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

Find out more about Guilford

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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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 29 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.