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 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Guilford vacation rentals

Terrace/patio

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.
$575 nightly
The price is $651
Sep 30 - Oct 1
Total with taxes and fees
Historic New England home ,Reunions Beach pass
TV, books

2. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (95 reviews)
"Great cottage on the Sound!"
United States
David S.
$872 nightly
The price is $993
Sep 28 - Sep 29
Total with taxes and fees
Direct waterfront renovated cottage.
Desk, laptop workspace, bed sheets

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, (189 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
$169 nightly
The price is $194
Sep 21 - Sep 22
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Living area

4. 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
$159 nightly
The price is $181
Sep 21 - Sep 22
Total with taxes and fees
Cozy 1-bedroom apartment in peaceful Branford with AC and gym access
Coffee/tea maker, fridge, microwave, oven

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, (28 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
$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
Interior

6. 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.
$417 nightly
The price is $472
Sep 20 - Sep 21
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Outdoor dining

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

Steps to Beach • Hot Tub • Game Room • Water Views
Branford
$1,142 nightly
The price is $1,292
Sep 20 - Sep 21
Total with taxes and fees
Steps to Beach • Hot Tub • Game Room • Water Views
Dining

8. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Great host and property"
United States
Kevin K.
$463 nightly
The price is $524
Sep 20 - Sep 21
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
Beach

9. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
$585 nightly
The price is $662
Sep 23 - Sep 24
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Flat-screen TV

10. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (56 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
$273 nightly
The price is $312
Oct 18 - Oct 19
Total with taxes and fees
North Fork Resort
Smart TV, books

11. 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.
$453 nightly
The price is $512
Sep 27 - Sep 28
Total with taxes and fees
Clear LI Sound waterview, Wedding pics, Yale&Beach
Coffee/tea maker, fridge, microwave, oven

12. Coastal Landing Stay

Coastal Landing Stay
East Shore
$468 nightly
The price is $507
Sep 20 - Sep 21
Total with taxes and fees
Coastal Landing Stay
Marina

13. 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.
$295 nightly
The price is $320
Sep 21 - Sep 22
Total with taxes and fees
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Interior

14. 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.
$912 nightly
The price is $1,032
Sep 20 - Sep 21
Total with taxes and fees
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Exterior

15. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (8 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
$294 nightly
The price is $333
Sep 20 - Sep 21
Total with taxes and fees
Angelica’s safe haven @ west haven
Condo | Terrace/patio

16. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (292 reviews)
"Great place!"
United States
Christine
$372 nightly
The price is $426
Oct 5 - Oct 6
Total with taxes and fees
Cliffside Resort Condominiums
Interior

17. VintageGem: Prime East Rock 5 mins to Yale 5 beds

VintageGem: Prime East Rock 5 mins to Yale 5 beds
East Rock
9.4 out of 10, Exceptional, (3 reviews)
"Met all expectations and the location is excellent."
United States
James D.
$371 nightly
The price is $418
Sep 21 - Sep 22
Total with taxes and fees
VintageGem: Prime East Rock 5 mins to Yale 5 beds
Exterior

18. Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
East Rock
10.0 out of 10, Exceptional, (11 reviews)
"Our 2 night stay was great. We were there for daughter's graduation from University of New Haven. Neighborhood was so quaint with lots of places to walk to. Place was very clean and accommodating. We would stay again!"
United States
Kathryn C.
$418 nightly
The price is $473
Oct 13 - Oct 14
Total with taxes and fees
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
Dining

19. 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, Wonderful, (28 reviews)
"Great value very close to university. "
United States
Lawrence
$196 nightly
The price is $222
Sep 20 - Sep 21
Total with taxes and fees
Stocked home close to Yale, in Heart of New Haven
Terrace/patio

20. The Jewel of The Cove - Historic Coastal Retreat

The Jewel of The Cove - Historic Coastal Retreat
East Shore
10.0 out of 10, Exceptional, (13 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.
$681 nightly
The price is $739
Oct 10 - Oct 11
Total with taxes and fees
The Jewel of The Cove - Historic Coastal Retreat
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

Motel 6 Milford, CT

Motel 6 Milford, CT

10/10 Excellent
"B"
Stephanie 2-night trip
Posted 5 hours ago
Motel 6 Milford, CT

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 $194 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.

Explore a world of travel with Expedia

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.