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

Holiday Rentals in Guilford

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Our top choices for Guilford holiday 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 €504
includes taxes & fees
30 Aug - 31 Aug
Historic New England home ,Reunions Beach pass

2. NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The house has a cozy, homey feel and was a nice place to come back to after being out for the day. It was quiet, comfortable, and had a relaxed vibe that made the trip easy.The location was a big plus for us. Hammonasset Beach was only a few minutes away, and Madison center was just as close, which made it easy to grab dinner or pop out for anything we needed. The outdoor fireplace was also a really nice touch and made the evenings feel special.Overall, it was a...
United States
Moe B.
The price is €326
includes taxes & fees
11 Aug - 12 Aug
NEW Coastal Cottage 2 Miles to Beach + Lake Access

3. 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, (177 reviews)
"Beautiful view, very clean !"
United States
Karolyne
The price is €223
includes taxes & fees
8 Sept - 9 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (281 reviews)
"Great place!"
United States
Christine
The price is €380
includes taxes & fees
9 Sept - 10 Sept
Cliffside Resort Condominiums

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, (26 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is €312
includes taxes & fees
1 Sept - 2 Sept
The gardners Cottage 1 mile from long Island Sound - pet friendly

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 €533
includes taxes & fees
23 Aug - 24 Aug
Clear LI Sound waterview, Wedding pics, Yale&Beach

7. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (45 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is €318
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort

8. The Jewel of The Cove - Historic Coastal Retreat

The Jewel of The Cove - Historic Coastal Retreat
East Shore
10.0 out of 10, Exceptional, (12 reviews)
"This was a great place to stay in New Haven, and a lot of care has gone into making it a welcoming house."
United States
Geoffrey H.
The Jewel of The Cove - Historic Coastal Retreat

9. 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 €295
includes taxes & fees
11 Aug - 12 Aug
Angelica’s safe haven @ west haven

10. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay"
United States
JM B.
The price is €191
includes taxes & fees
9 Sept - 10 Sept
1-bedroom cottage with Grove Beach 🏖️ access.

11. Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (10 reviews)
"Easy check in and was as described. It was perfect for our needs for a place to stay over the holidays."
United States
Danielle D.
Cozy East Haven Home • Near Beach & Yale

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

Steps to Beach • Hot Tub • Game Room • Water Views
Branford
The price is €1,166
includes taxes & fees
8 Sept - 9 Sept
Steps to Beach • Hot Tub • Game Room • Water Views

13. 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
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is €902
includes taxes & fees
11 Aug - 12 Aug
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

14. Coastal Landing Stay

Coastal Landing Stay
East Shore
The price is €449
includes taxes & fees
12 Aug - 13 Aug
Coastal Landing Stay

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

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (16 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is €387
includes taxes & fees
11 Aug - 12 Aug
Adorable Cottage, 5 min walk to water & town

16. Relaxing 3-bedroom apartment in New Haven

Relaxing 3-bedroom apartment in New Haven
New Haven
9.4 out of 10, Exceptional, (3 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.
The price is €336
includes taxes & fees
11 Aug - 12 Aug
Relaxing 3-bedroom apartment in New Haven

17. 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 €196
includes taxes & fees
12 Aug - 13 Aug
Stocked home close to Yale, in Heart of New Haven

18. Brand New Home Close To Yale!

Brand New Home Close To Yale!
The Hill
10.0 out of 10, Exceptional, (4 reviews)
"The place was very clean and had every essential needed. Not to mention, the proximity to downtown and Union Station were a huge bonus"
United States
Marcel D.
The price is €284
includes taxes & fees
11 Aug - 12 Aug
Brand New Home Close To Yale!

19. 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
The price is €157
includes taxes & fees
8 Sept - 9 Sept
Cozy 1-bedroom apartment in peaceful Branford with AC and gym access

20. Heavenly Home in New Haven /5 mins drive from Yale

Heavenly Home in New Haven /5 mins drive from Yale
Fair Haven
9.2 out of 10, Wonderful, (23 reviews)
The price is €577
includes taxes & fees
23 Aug - 24 Aug
Heavenly Home in New Haven /5 mins drive from Yale
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

Everything you need to know about Guilford holiday rentals

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

Guilford holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Guilford holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Guilford holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Guilford rentals

At Expedia, we put the best Guilford holiday 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 holiday.

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. 

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! A Reunion/Retreat/Event 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 30 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 Guilford Art Center.

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.