Guilford vacation rentals

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Popular amenities for Guilford vacation rentals

Stay near Guilford's top sights

Bishop's Orchards Farm Market & Winery57 locals recommend
The Place Restaurant31 locals recommend
Thimble Islands26 locals recommend
Quattro's Italian Restaurant25 locals recommend
Guilford Town Green21 locals recommend
Henry Whitfield State Museum20 locals recommend

Other great vacation rentals in Guilford

Top guest favorite
A serene view of a private lake is captured during twilight, with gentle colors reflected on the water's surface. A stone bench is visible in the foreground, accompanied by a potted plant, and lush green grass leads to the lake's edge.
Home in Andover
4.98 out of 5 average rating, 55 reviews

Spacious Classic Lakefront Home with jet tub

CasimirRating, 5 stars3 months ago
I came here in the dead of winter for a writer's retreat with a fellow writer- AND I WOULD DO IT AGAIN! It was a beautiful and inspiring place to write. Perched on Andover Lake, it was too cold to frolic outside but that was actually liberating. There was a rocking chair-ottoman combo in the master bedroom looking out on the lake and watching it freeze while I worked on some writing was so peaceful and perfect. When I needed to switch it up, there was a writer's desk with the same view and I can not overstate how nice and productive it was to work from it. I am sure in the summer it's a really fun stay (there were kayaks and a dock for swimming) but I actually loved being isolated in such an idyllic place. It's near a few other homes but the road was low traffic enough for a cold weather run around half the lake. Marcie was super helpful with suggestions for places to eat. We didn't actually use the recs - but that only speaks to how nice the house was and how hard it was to leave!
Top guest favorite
Cottage in Guilford
4.99 out of 5 average rating, 136 reviews

"Red House on the Knoll" at Indian Cove

MaryRating, 5 stars1 week ago
My family and I loved staying at Gail’s place! We grew up in Madison and were back for a visit. It was such a great place and allowed us to re-live many fond memories of growing up in the area!
Guest favorite
A waterfront balcony is featured, showcasing wood paneling and a clear view of the water. The deck is equipped with a railing and lights, offering a relaxing spot to enjoy the scenery. The sunlight casts shadows along the planks, highlighting the serene environment.
Home in North Fork
5 out of 5 average rating, 9 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

KristinaRating, 5 stars2 days ago
Had a wonderful time over Easter with my family and dog. The view was exquisite and the house very comfortable. Eileen was very responsive and even had hair dryers sent over. The house was very well equipped with lots of kitchen staple goods. Just be aware there is no microwave, but there is a very nice Breville toaster oven. Also, there is a large table outside for a group, but only a small table and counter seating in kitchen inside. We didn't have any issue since the weather was perfect for us to enjoy our Easter dinner outside. Overall, a beautiful home and only minutes from Greenport and wineries.
Top guest favorite
The serene cabin is surrounded by tall trees and lush greenery, providing a peaceful retreat. A wooden dock extends into the calm water, reflecting the cottage's exterior. A screened-in porch adorned with outdoor furniture can be seen, inviting relaxation and enjoyment of the natural setting.
Bungalow in Old Lyme
4.94 out of 5 average rating, 306 reviews

Pet Friendly Bungalow!!!

BrittanyRating, 5 stars2 days ago
June and her bungalow emanated an inviting warmth from the very beginning. My partner and I were looking for a peaceful getaway with our pup, and we were thrilled to see such a beautiful, affordable, pet friendly option by the water. I then saw that it was just 15mins from my grandmother in Waterford, so we would be able to visit with her, too! We exchanged friendly messages right after booking, and I immediately felt confident and comfortable with our decision to stay at her place. June was incredibly thoughtful and seemed to think of everything! She sent a message earlier in the week ahead of the booking to let us know she was preparing for our stay and to share excitement on the beautiful forecast. She was flexible and communicative on check in/check out times, and wished us well throughout her stay. We felt truly at home upon arrival. You can tell this bungalow has been loved and cared for, and that many good times have been shared. Very positive and serene energy. 🌅♥️🐾
Guest favorite
A large beach house is visible, featuring multiple gables and a spacious deck with balcony. The facade is painted in light grey, complemented by white trim. In the foreground, sandy beach leads toward the house, framed by green grass and shrubs on either side.
Home in West Haven
4.95 out of 5 average rating, 19 reviews

Beach House steps from sand & Amazing Views

DonnaRating, 5 stars1 week ago
Beautiful home with lovely views. Great kitchen for cooking. We had 8 of us and the house was spacious and welcoming for the group.
Superhost
A serene beach scene captures gentle waves lapping at smooth stones along the shoreline. Soft, sandy areas are visible in the distance, with greenery lining the coast. A cloudy sky provides a soft light over the tranquil waters.
Home in Waterford
4.94 out of 5 average rating, 18 reviews

Summer Beach Cottage Harknes, Ocean Beach N

JenniferRating, 5 stars7 months ago
It was a perfect spot for our little family vacation. We were so close to a few really nice beaches and the area is a short drive to mystic aquarium and village. Patsy and family are very nice and gave some great suggestions for activities in the area.
Guest favorite
A spacious outdoor area is highlighted by a refreshing pool surrounded by lounge chairs. The pool house, featuring a white exterior, sits in the background amidst lush greenery. Flower pots and garden plants frame the scene, enhancing the tranquil environment.
Guesthouse in Shelter Island
4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House

YuryRating, 5 stars11 months ago
Perfect getaway in Shelter Island! The pool house is as amazing as it looks in the listing :) Cute house on a beautiful, peaceful and very private green lot. Primael was very welcoming and responsive. She was also very flexible in terms of our check in and check out. Everything went super smoothly. We enjoyed our stay a lot!
Guest favorite
A charming beachside home is showcased, featuring a wrap-around porch with seating. The sandy beachfront extends along the water's edge, and a clear blue sky overhead enhances the coastal atmosphere. Nearby houses are visible, offering a sense of community along the shore.
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars3 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!

Quick stats about vacation rentals in Guilford

  • Total rentals

    100 properties

  • Total number of reviews

    6.3K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    100 properties include access to wifi

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Guilford?

    Yes! Work meets play with ease at over 60 vacation rentals in Guilford featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Guilford?

    Four-legged friends are welcome in Guilford. Choose from more than 40 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in apartment rentals in Guilford?

    Experience the best of Guilford with our apartment rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do cottage rentals in Guilford have wifi?

    Absolutely! We offer over 10 cottage rentals with wifi in Guilford. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Guilford have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Guilford. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Guilford have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Guilford. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Guilford?

    Guilford has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Apartment Rentals in Guilford?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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  4. New Haven County
  5. Guilford