Guilford Vacation Rentals

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Our top choices for Guilford vacation rentals

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.
$440 nightly
The price is $499
May 19 - May 20
Total with taxes and fees
Historic New England home ,Reunions Beach pass

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (151 reviews)
"I loved the location and the view!"
United States
Gabrielly
$175 nightly
The price is $201
Jun 17 - Jun 18
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
$239 nightly
The price is $274
Jun 7 - Jun 8
Total with taxes and fees
Cliffside Resort Condominiums

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (17 reviews)
"Great stay & great staff!"
United States
James
$199 nightly
The price is $228
May 19 - May 20
Total with taxes and fees
North Fork Resort

The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes

The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes
East Shore
10.0 out of 10, Exceptional, (3 reviews)
"This is a nice spot to enjoy the Long Island Sound."
United States
Susan N.
$526 nightly
The price is $596
May 25 - May 26
Total with taxes and fees
The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes

Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
8.8 out of 10, Excellent, (6 reviews)
"Great host and property"
United States
Kevin K.
$410 nightly
The price is $464
May 19 - May 20
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (16 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
$275 nightly
The price is $312
Jun 4 - Jun 5
Total with taxes and fees
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (11 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
$879 nightly
The price is $994
May 20 - May 21
Total with taxes and fees
Clear LI Sound waterview, Wedding pics, Yale&Beach

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
$319 nightly
The price is $343
May 19 - May 20
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (36 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
$274 nightly
The price is $311
May 26 - May 27
Total with taxes and fees
Walk To Goodspeed Opera House!

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
$356 nightly
The price is $403
May 19 - May 20
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Killingworth
10.0 out of 10, Exceptional, (56 reviews)
"Stayed here for Valentine's weekend with my wife and it was perfect! Gardner and Kathy were great with communication and the cabin itself was beautiful! It had everything we needed for the weekend and the location is close to many nearby attractions. Book your stay at Mapletree Cabin.. you won't regret it! "
United States
Miguel D.
$726 nightly
The price is $821
Jun 3 - Jun 4
Total with taxes and fees
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

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, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$274 nightly
The price is $292
May 19 - May 20
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$233 nightly
The price is $264
May 19 - May 20
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
$394 nightly
The price is $445
May 19 - May 20
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA

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.
$281 nightly
The price is $319
May 19 - May 20
Total with taxes and fees
Angelica’s safe haven @ west haven

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (42 reviews)
"Extremely cozy, comfortable and clean! Really impressed after walking through the door...details of flowers, fruit, water, and coffee and tea. Pleasantly Surprised and would definitely stay again and recommend. Thank you!!"
United States
Kristen B.
$182 nightly
The price is $206
May 19 - May 20
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Westbrook Center
9.4 out of 10, Exceptional, (3 reviews)
"We had a lovely time during our stay. The hosts were excellent with communication and quick responses throughout our stay. The 2 family suites were perfect for our families to all stay together during this trip. We would definitely book again! "
United States
Kate G.
$673 nightly
The price is $761
May 19 - May 20
Total with taxes and fees
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

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.
$331 nightly
The price is $361
Jun 1 - Jun 2
Total with taxes and fees
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

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
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
Australia
Nina
$400 nightly
The price is $452
Jun 2 - Jun 3
Total with taxes and fees
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/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 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 $201 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.

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! A Reunion/Retreat/Event estate! JULY OPENINGS 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 28 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 Guilford Art Center.

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.