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Guilford vacation rentals

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Top-rated vacation rentals in Guilford

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Cottage in Guilford

4.95 out of 5 average rating, 173 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Cottage in Guilford

4.93 out of 5 average rating, 264 reviews

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Rental unit in Middletown

4.94 out of 5 average rating, 754 reviews

Quaint 2br apt- 1 block walk to Wesleyan & Main St

Nicely appointed 1st floor 2 BR apt with mid-century modern inspired decor that is a cozy home away from home. House is 1 block from Wesleyan and 2 blocks from food/fun on Main St, so you don’t need to use your car to visit Wesleyan or get to anything in town since the location is very walkable. Laundry, dishwasher, tv with roku, dvd player and dvd’s, books, bluetooth radio, wifi, front porch and back yard seating, close to Rt 9, I-91, Rt 84, Hartford and short drive to beaches/shoreline/I-95.

Rental unit in Guilford

4.99 out of 5 average rating, 269 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

Cottage in Westbrook

4.87 out of 5 average rating, 128 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Home in Branford

4.98 out of 5 average rating, 107 reviews

Beach Cottage by the Sea - Only 10 min from I-95

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

Yurt in Guilford

4.88 out of 5 average rating, 115 reviews

Hartwoods Yurt

Enjoy a unique wilderness getaway and unwind in a peaceful wooded environment in our 30’ diameter Yurt, which sleeps 4 in North Guilford, CT. This elevated cylindrical dwelling offers solitude and a large deck with comfortable chairs and forest views. Shaded and cool in the summer with air conditioning and fans available. This Yurt provides a wonderful respite from the hectic world. Perfect for nature lovers with a nearby brook and miles of trails for hiking and mountain biking.

Guesthouse in Portland

4.99 out of 5 average rating, 149 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Home in Haddam

5 out of 5 average rating, 101 reviews

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Home in Branford

4.95 out of 5 average rating, 103 reviews

Charming home, easy access to everything Branford

Full home, comfortable and very well equipped. Private fenced in backyard with patio dining area. Off-street (driveway) parking. Short Walk to the Shoreline Greenway trail. Less than a mile to downtown, parks, beaches, restaurants, marina, Stoney Creek Brewery. Near event venues, The Owenego and Pine Orchard club. Close to New Haven. Family(kid) Friendly home with private fenced in backyard with patio dining area. Equipped with Pack N Play, highchair, booster seat, etc

Rental unit in East Haddam

4.9 out of 5 average rating, 149 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

Guest suite in Wallingford

5 out of 5 average rating, 540 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

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Popular amenities for Guilford vacation rentals

Laptop-friendly workspace

Air conditioning

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

Rental unit in Branford

4.94 out of 5 average rating, 17 reviews

Stony Crk Studio ideal for trvl nurses…

Home in Guilford

5 out of 5 average rating, 23 reviews

Charming 2BR Beach House Overlooking the Water

Cottage in Guilford

4.99 out of 5 average rating, 96 reviews

Waterfront Joshua Cove Cottage with private beach.

Home in Guilford

5 out of 5 average rating, 47 reviews

Coastal Farmhouse walking distance to town

Guesthouse in Guilford

4.99 out of 5 average rating, 92 reviews

Guilford Lakes Cottage, with hot tub and fire pit.

Rental unit in Guilford

5 out of 5 average rating, 40 reviews

Historic 2 bdrm apartment in downtown Guilford

Rental unit in Guilford

4.92 out of 5 average rating, 52 reviews

The Leete House a taste of Historic Guilford

Guesthouse in Clinton

4.96 out of 5 average rating, 25 reviews

Studio Cottage

Quick stats about vacation rentals in Guilford

Total rentals
110 properties
Total number of reviews
6.1K 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
110 properties include access to wifi

Frequently Asked Questions

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.
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.
Do apartment rentals in Guilford have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Guilford. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in cottage rentals in Guilford?
Experience the best of Guilford with our cottage rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly cottage rentals in Guilford?
Guilford has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cottage rentals in Guilford have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Guilford. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Guilford have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Guilford. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cottage Rentals in Guilford?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a bbq area, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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