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 CA $350
CA $810 total
includes taxes & fees
Aug 30 - Aug 31
Historic New England home ,Reunions Beach pass

2. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
The price is CA $221
CA $512 total
includes taxes & fees
Aug 24 - Aug 25
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $221
CA $392 total
includes taxes & fees
Aug 19 - Aug 20
1-bedroom cottage with Grove Beach 🏖️ access.

4. 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, (173 reviews)
"Beautiful view, very clean !"
United States
Karolyne
The price is CA $202
CA $361 total
includes taxes & fees
Aug 30 - Aug 31
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

5. 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, (25 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is CA $350
CA $584 total
includes taxes & fees
Aug 20 - Aug 21
The gardners Cottage 1 mile from long Island Sound - pet friendly

6. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.0 out of 10, Wonderful, (14 reviews)
"Conveniently located and nice, practically appointed stay for a business trip to work with a collaborator in town."
United States
Jeremy Y.
The price is CA $151
CA $341 total
includes taxes & fees
Aug 2 - Aug 3
Bright Downtown Studio near Yale & East Rock!

7. Modern Studio Retreat

Modern Studio Retreat
Dwight
10.0 out of 10, Exceptional, (1 review)
The price is CA $183
CA $304 total
includes taxes & fees
Aug 7 - Aug 8
Modern Studio Retreat

8. Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University
Fair Haven
6.8 out of 10, (3 reviews)
"Blankets where itchy and smelled dirty small room when whole house was listed"
United States
Isabella R.
The price is CA $110
CA $154 total
includes taxes & fees
Aug 12 - Aug 13
Cozy 1-bedroom house in lovely New Haven with AC close to Yale University

9. 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 CA $165
CA $410 total
includes taxes & fees
Aug 1 - Aug 2
Once the old Schools house now a newly furnished Apartment

10. Cozy Stay by Little Italy & Wooster Street

Cozy Stay by Little Italy & Wooster Street
Mill River
10.0 out of 10, Exceptional, (2 reviews)
"This apartment in a 4 unit building with its own parking lot was on a quiet street. Easy to get to no matter what side of the city I came from and close enough to walk to downtown (6 blocks) and half a block off the famous Little Italy street for food and cocktails and then brunch and coffee in walking distance in the mornings too. The unit had everything you need, fully stocked kitchen and bath, shared laundry. Great mattress and pillows! Easy keypad entry. I’d stay there over and over again!"
United States
Erica S.
The price is CA $167
CA $437 total
includes taxes & fees
Aug 2 - Aug 3
Cozy Stay by Little Italy & Wooster Street

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

Stocked home close to Yale, in Heart of New Haven
Mill River
9.2 out of 10, Wonderful, (27 reviews)
"Great value very close to university. "
United States
Lawrence
The price is CA $176
CA $317 total
includes taxes & fees
Aug 12 - Aug 13
Stocked home close to Yale, in Heart of New Haven

12. 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 CA $132
CA $284 total
includes taxes & fees
Aug 26 - Aug 27
One bedroom in United States of America, New Haven

13. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is CA $203
CA $489 total
includes taxes & fees
Aug 6 - Aug 7
Angelica’s safe haven @ west haven

14. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
United States
Linda v.
The price is CA $165
CA $410 total
includes taxes & fees
Aug 1 - Aug 2
Newly Remodeled 1-BR Close to Everything yet Very Private

15. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is CA $165
CA $406 total
includes taxes & fees
Aug 26 - Aug 27
All New Studio apartment in center of town

16. Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is CA $165
CA $407 total
includes taxes & fees
Aug 3 - Aug 4
Newly Remodeled with deck. Close to town center

17. Château Blanc | Near Yale University

Château Blanc | Near Yale University
Dwight
8.6 out of 10, Excellent, (9 reviews)
"Perfect for a quick trip and one night stay!"
United States
Chris D.
The price is CA $122
CA $283 total
includes taxes & fees
Aug 3 - Aug 4
Château Blanc | Near Yale University

18. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is CA $165
CA $407 total
includes taxes & fees
Aug 12 - Aug 13
All New 1BR with tons of Charm

19. Bright Downtown New Haven Escape

Bright Downtown New Haven Escape
Downtown New Haven
9.8 out of 10, Exceptional, (6 reviews)
"In the heart of downtown New Haven and convenient to everything."
United States
Stewart C.
The price is CA $167
CA $456 total
includes taxes & fees
Aug 12 - Aug 13
Bright Downtown New Haven Escape
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! A Reunion/Retreat/Event 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 Sachem Head Harbor.

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.