Holiday rentals in Guilford

4.95 out of 5 average rating, 181 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)

4.96 out of 5 average rating, 50 reviews

Flat in Guilford

Enjoy a taste of New England Charm

Enjoy a taste of New England charm, located by the historic Guilford Green. Wonderful restaurants, great shopping, Long Island Sound, beach, parks and train within walking distance. Hike/ mountain bike 1200 acres in nearby Westwoods. Tour historic homes or take a Segway or walking tour. Explore Long Island Sound by boat, beaches or walking the shoreline. Local golf, dog parks & more. The home boasts spacious rooms. Newly remodeled kitchen & bath. Use of backyard & deck. Immaculate interior

4.99 out of 5 average rating, 497 reviews

Guest house in Guilford

Get Back to Nature at a Modern Wood Clad Getaway

SPRING IS HERE--Glorious spring birds. Come and enjoy a wonderful time in our guest house--warm days, cool nights. You can Hike on the trails, and Stroll along the ocean. Ospreys; hawks; cardinals, blue jays, bluebirds, gold finches and more are here year round. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

4.99 out of 5 average rating, 97 reviews

Holiday home in Guilford

Spacious Oceanfront Getaway with Spectacular Views

Perfect vacation getaway! Awaken to the sun rising over Long Island Sound! Panoramic waterfront views from 70 ft of windows spanning NY to RI. Quiet, private, updated home, NOT a cottage: >2200 sq ft, single level 3B/3B, + bonus lower-level walk-out/office. Master bed double shower/jacuzzi overlooking the water! Multiple oceanfront decks. 100 ft granite shoreline, short stroll to nearby sand beaches. Swim, fish, read a book, or watch the sailboats go by! (Not suitable for children/pets/events.)

4.93 out of 5 average rating, 273 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”.

4.99 out of 5 average rating, 275 reviews

Flat in Guilford

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.

4.88 out of 5 average rating, 163 reviews

Cottage in Westbrook

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.

5 out of 5 average rating, 13 reviews

3BR Waterfront Oasis on Joshua Cove, Private Beach

Kick back and relax in this modern, stylish waterfront home with a private beach. Newly renovated, this house offers beautiful, unobstructed views of the Long Island Sound and a backyard equipped with an outdoor patio & dining area, hammock, firepit, adirondack chairs, chaise lounges, and cushioned outdoor furniture (in season). You can enjoy swimming at the home's private beach in summer, leaf-peeping in fall, and bird watching in spring. The house is located 5 minutes from downtown Guilford.

4.96 out of 5 average rating, 84 reviews

Flat in Guilford

Cozy Private Lake Q Retreat

Escape to a charming lakeside haven! Our cozy 1-bed, 1-bath retreat is a tranquil getaway. Nestled by the water, it's perfect for a romantic escape or a solo recharge. Enjoy stunning lake views, a comfy bedroom, and a serene bathroom. Unwind on the private deck, take a dip in the crystal-clear waters, or explore nearby nature trails. A lofted office space with l-shaped desk and computer monitor with connection hub invites both creativity and productivity. Your lakeside escape awaits!

4.99 out of 5 average rating, 110 reviews

Flat in Branford

Downtown Branford Retreat - Quiet yet Central Apt

A welcoming apartment nestled in the heart of Branford - a quintessential shoreline community! This inviting space offers modern design, a well-equipped kitchen, comfortable bedroom, and a convenient location. Situated within walking distance of the town green and minutes from beaches, guests can easily explore this vibrant shoreline town. From boutique shops and art galleries to charming cafes and trendy restaurants, experience the best of Branford right at your doorstep!

4.94 out of 5 average rating, 269 reviews

The Cottage at Indian Cove

A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

4.96 out of 5 average rating, 157 reviews

Guest suite in Guilford

Bright, Cozy Apartment in Guilford

Welcome to Guilford! Our cozy, private apartment has everything you need for a relaxing stay in Guilford. Swim in the pool or explore the hiking trails behind the property! If you'd like to explore further, we are a 10 minute drive from the center of town, and a 25 minute drive to New Haven. Featured Amenities: Pool Free Off-Street Parking Private Entrance Grill and Outdoor Seating Hiking Trails

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Other great holiday rentals in Guilford

4.97 out of 5 average rating, 35 reviews

Home in Branford

Adorable Beach House on LI Sound

JudyRating, 5 stars3 days ago

We had a wonderful stay at Eileen’s place. Many great restaurants close by…Lenny’s, Dockside and Rosso Vino we enjoyed. Delicious ice cream spots..Bishop’s Orchard Creamery and Ashley’s.

4.95 out of 5 average rating, 80 reviews

Direct Shoreline Long Island Sound Waterfront

ThomasRating, 5 stars9 months ago

Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.

Superhost

4.88 out of 5 average rating, 51 reviews

The Davis House

PhilipRating, 5 stars3 weeks ago

we have stayed at this place multiple times. It is very conveniently located near our kids and also very easy to get to. It is spacious and comfortable and clean. The house is a bit on the “vintage” side, but that shouldn’t matter, and it contains pretty much everything you could want as a guest in a house. It is a little on the pricy side, but if you need three bedrooms and three bathrooms, it is a good value. And Sharon is very responsive. She does have particular rules and expectations, but nothing more than should be expected of a good guest in someone’s house. (as opposed to being a hotel guest where you don’t need to clean up after yourself) we strongly recommend this place.

5 out of 5 average rating, 51 reviews

Coastal Farmhouse walking distance to town

KathleenRating, 5 stars2 weeks ago

Mario’s place was beautifully renovated and outfitted perfectly making us feel right at home. Actually the home was furnished, cleaned and stocked better than most peoples primary homes! We’re ocd clean people and travel with our own cleaning products but that was completely not needed in Mario’s place. It was spotless! Even the washer/dryer were like new which we took advantage of during our stay. Traveling with seniors, infant and young toddler, we appreciated the home was baby safe and had kids games and toys. Love that the home was well thought out for guests and included plenty of paper products, plush linens, soaps, towel racks in every bedroom. etc. beds and furniture were both very comfy. This location is perfect and serene. We honestly would have been very comfortable staying for a much longer trip. Close to town with delicious food and lovely shops. Easy access to the highway too. We were all around impressed with this rental..One of our favorite airbnbs to date!

Yurt in Guilford

4.86 out of 5 average rating, 125 reviews

Hartwoods Yurt

AlexRating, 5 stars3 weeks ago

We stay here often, and always find something new to appreciate. It's been a chilly spring, but thankfully, the wood stove kept us all cozy. Being up in the trees, we could hear so many unique birds! We usually cook, but found the local restaurants in Guilford to be quite good. I say it every time, but it's always the getaway my family needs with the right amount of nature to escape, without sacrificing too many creature comforts. It's our happy place!

4.99 out of 5 average rating, 69 reviews

Flat in Clinton

Cozy Shoreline Getaway

HowardRating, 5 stars1 month ago

Second time staying at this Airbnb. Excellent hosts, conveniently located, and cottage had all the amenities.

5 out of 5 average rating, 7 reviews

Mulberry Seaside Cottage

EmilyRating, 5 stars3 weeks ago

This home was exactly as described and pictured. The home is tastefully decorated and comes with everything you need. Not to mention the beautiful views, the easy walks to either beach, and bikes in the basement to explore the neighborhood. You will not be disappointed with Carol's place! Even with unpredictable weather we still had a great restful vacation! I would book here again!