Vacation rentals in Guilford

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

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)

4.99 out of 5 average rating, 496 reviews

A modern living space features a comfortable sofa, a circular coffee table, and a television unit. Large sliding glass doors create a seamless view of the outdoors, with natural greenery visible beyond the private deck. Soft natural light fills the room, enhancing its inviting ambiance.

Guesthouse 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.

Vacation home in Guilford

A spacious living room features dramatic oversized picture windows providing unobstructed water views. A granite fireplace stands beside a leather couch adorned with comfortable pillows. Two leather chairs offer reclining options, and a central table complements the inviting ambiance.

4.99 out of 5 average rating, 97 reviews

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.)

A serene waterfront view features a grassy area leading to a calm body of water. A white chair stands prominently on the shore, with a distant view of charming homes lining the opposite bank under a clear blue sky with scattered clouds.

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, 274 reviews

A serene coastal scene showcases a calm shoreline reflecting a vibrant sunset. Soft clouds ripple across the sky, transitioning from orange to purple, while the water mirrors these colors. Bare trees outline the background of a quaint beach, blending seamlessly with the tranquil setting.

Apartment 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.

4.95 out of 5 average rating, 100 reviews

A spacious living area features a large, comfortable sofa facing a stone fireplace with a modern television mounted above it. A skylight allows natural light to brighten the room, and an open kitchen is visible in the background with sleek cabinetry and barstool seating.

Guesthouse in Guilford

Guilford Lakes Cottage, with hot tub and fire pit.

Kick back and relax in this calm, stylish home, yards from private lakes for kayaking, swimming, fishing or skating in season. For the adventurer, enjoy year round access to extensive forest trail systems for hiking, mountain biking, cross country skiing, and snowshoeing, only a 2 minute walk from our door. Nicknamed " Guilford's Little Augusta," the 9 hole, par 27 executive Guilford Lakes Golf Course is only 1/4 mile away. Five miles south lies one of the 5 most beautiful town greens.

4.96 out of 5 average rating, 83 reviews

A calm lake reflects the soft hues of twilight, bordered by lush greenery on both sides. The water's surface is smooth, mirroring the trees and the sky above. A faint crescent moon can be seen as it begins to rise in the background.

Apartment 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, 89 reviews

An outdoor patio area features a mix of seating options, including two lounge chairs and a cushioned armchair, arranged on stone flooring. String lights are draped overhead, and a barbecue grill is positioned nearby. Lush greenery surrounds the space, enhancing the calm ambiance.

Guesthouse in Guilford

Page Guest House

Updated, private detached guest house in the center of Guilford's historic district just steps from the town center. The guest house is completely renovated. Walk to everything including shops and restaurants. Town Beach and doc are just under 1.5 miles away. The second bedroom has a twin bed. You have to walk through twin room to get to master. Apartment is one floor with no steps. Bathroom is tiled and shower is walk in with no lip or tub and is easily accessible.

An aerial view captures the cottage's proximity to the beach, with sandy shores and gentle waves visible. The surrounding area features a blend of trees and homes, enhancing the scenic coastal environment.

4.94 out of 5 average rating, 268 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.

4.97 out of 5 average rating, 102 reviews

A wooden playset is situated in a spacious backyard, featuring a slide, swings, a climbing structure, and a fort-like space with a roof. Surrounding it are tall evergreen trees, adding a natural backdrop to the play area. The ground is covered in wood chips for safety.

Guesthouse in Madison

Beachy & Bright Coastal Escape - 5 Mins to Beach

Charming coastal guesthouse in Madison’s historic district—just a 5-min walk to a private beach, 5-min drive to town, and 20 mins to New Haven. Bright, beachy, and newly renovated with a king bedroom, full kitchen, private deck, and huge backyard. Set on nearly an acre in the heart of New England, it’s perfect for couples, families, and girls’ getaways. Walk to cafes, shops, and the iconic RJ Julia bookstore.

Guest suite in Wallingford

A lush garden space is surrounded by vibrant greenery and flowering plants. A brick patio features a red umbrella over a small table and chairs, providing a shaded area for relaxation. Decorative planters enhance the tranquil setting, inviting guests to enjoy the outdoors.

5 out of 5 average rating, 591 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.

4.96 out of 5 average rating, 157 reviews

A sparkling pool features clear blue water with gentle ripples. The pool's edge is lined with a textured white finish, emphasizing a clean and inviting space. The surrounding area is paved, providing a spacious setting for relaxation.

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 vacation rentals in Guilford

4.94 out of 5 average rating, 70 reviews

Scenic Mulberry Point Connecticut Beach House

AndreaRating, 5 stars4 weeks ago

Michael and Marchen's house is in a lovely location right next to a pretty little beach; the house is airy, light, and very comfortable, and the views of the water from outdoors (and indoors!) are great. We were there for a graduation weekend, so didn't spend a lot of time hanging out at the house, but we would have enjoyed doing that, too. Kitchen was well-equipped; bathroom was clean and modern and pretty; beds very comfortable! Marchen was very responsive and helpful--all in all, a lovely stay and we'd stay again.

A screened-in porch offers views of the water and sandy beach, with natural light filtering through large windows. A patterned rug covers the floor, while a white wicker chair invites relaxation. The lush green lawn and shoreline are visible outside.

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 stars2 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.

An open interior space features a circular design with wooden beams converging at a skylight. Comfortable seating areas include two sofas and multiple chairs, complemented by a dining table. The warm wooden flooring enhances the inviting atmosphere, with natural light filtering through the windows.

Yurt in Guilford

4.86 out of 5 average rating, 124 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!

Superhost

4.72 out of 5 average rating, 140 reviews

Purple Button Factory Sleeps 6 Walk to Town Green

JulieRating, 5 stars4 weeks ago

Our family had a beautiful stay at the Purple Button Factory. Charming and comfortable, this historic house was perfect for exploring Guilford. A special nostalgic trip for us as my children grew up here. Short walk to wonderful cafes and shops on The Green. We loved the birdlife and views from the back patio and absolutely fell in love with the picturesque sunny kitchen. Spent a lot of time gathered together there around the wooden table. Than you for sharing your home.

A charming alleyway is lined with warm string lights, highlighting the entrance to South Lane Bistro. Colorful mums in orange and yellow pots complement the rustic decor. Brick pathways guide visitors through a quaint setting filled with greenery and inviting outdoor seating.

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!

A fox stands on a grassy area, partially obscured by a blurred feature. It is surrounded by dense greenery, with various shades of green leaves providing a natural backdrop. The fox's fur displays a mix of orange and brown tones, contrasting with the environment.

4.93 out of 5 average rating, 54 reviews

Guilford cozy in-law apt with private entrance

LalaRating, 5 stars3 weeks ago

beautifully decorated apartment! host was very drscriptive about the location, making it an eady checkin process. he was very accomodating to special requests as well. we had a nice and cozy stay!

A sunlit room features a large window area allowing natural light to fill the space. A comfortable sofa is positioned near a small table with a decorative lamp. A playful assortment of toys is organized in a nearby storage area, complemented by warm wooden flooring.