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Guesthouse vacation rentals in Middlesex County

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Top-rated guesthouse rentals in Middlesex County

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

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Guesthouse in Essex

4.78 out of 5 average rating, 18 reviews

Privateers Boathouse (Village Waterfront)

Right in the middle of everything Essex Village has to offer. Very special little waterfront cottage with unrivaled views & access to town is hosting guests. Park your car off-street and enjoy all the wonders of Essex Village by foot during your visit. Secluded, yet utterly central Village location. Short drive to beaches, golf, hikes & more. 🌟 Request a WEEKLY rate 🌟 🛶 Access to swimming pool, kayak/paddle board launch ONLY WITH ADVANCE ARRANGEMENT 🚣‍♀️

Sep 23 – 30

R6,851 ZAR per night

Guesthouse in East Hampton

4.83 out of 5 average rating, 42 reviews

Your Own Barn Loft Suite Among the Treetops

Forget your worries in this spacious and serene space. You’ll arrive through your own driveway, park in your own spot and enter through a private entrance. Make yourself at home whether a weekend get away or traveling for work you’ll feel very relaxed. 250’ from the airline trail, walk or bike right into downtown East Hampton for a coffee in the morning or set out on the 30 + mi trail to enjoy your true country getaway. Head into Middletown to enjoy many restaurants, bars or clubs. *NOTE PET FEE

Jan 21 – 28

R3,285 ZAR per night

Guesthouse in Chester

5.0 out of 5 average rating, 41 reviews

Delightful Cottage in Charming Chester

Enjoy all the Connecticut River Valley has to offer and use this newly renovated cottage as your relaxing home base. The cottage is a 2 min. drive (or 12 min. walk) to charming downtown Chester. There you will find delicious dining options, unique shops, galleries, a brewery and a theater. Chester is also home to a wonderful Sunday farmers market -mid June to mid October. Area attractions include Gillette Castle, Essex Steam Train, Florence Griswold Museum, CT River Museum and wonderful hiking.

Oct 30 – Nov 6

R4,018 ZAR per night

Guesthouse in Old Lyme

5.0 out of 5 average rating, 40 reviews

Studio Four-Entire Guesthouse near CT River

Take it easy at this unique and tranquil getaway. Studio Four offers an architecturally dynamic space flooded with light nestled into the landscape to embrace the pastoral surroundings. Close to the Connecticut River the property is private and offers its guests access to a private dock association on the Connecticut River at Goose Island, Lords Cove. You have access to a kayak launch and bikes, and can hike the neighborhood nature preserve which takes you to a scenic vista on the CT river.

Sep 22 – 29

R4,593 ZAR per night

Guesthouse in Guilford

4.99 out of 5 average rating, 76 reviews

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.

Aug 21 – 28

R12,953 ZAR per night

Guesthouse in Madison

4.97 out of 5 average rating, 69 reviews

Beachy & Bright Carriage House/5 min walk to Beach

Just 2 hrs from Boston/NYC, get away from it all w/this one a one of a kind, beautiful & spacious property. If you’re looking for a romantic weekend, girls getaway or a kid friendly space, you have found the perfect spot! Beach is 5 min walk, backyard is a kids paradise, 5 min drive to town. Antique shops, wineries, seafood restaurants all within 10 mins. Sit on private deck sipping coffee or wine and watch the sun rise or set. Hiking/biking/walking trails right out your front door.

Mar 7 – 14

R7,193 ZAR per night

Guesthouse in Madison

4.93 out of 5 average rating, 14 reviews

In-law apartment with Private entrance

Welcome to our charming in-law apartment, the perfect retreat for your mini getaway. Nestled in a central location, our cozy space offers easy access to all that the area has to offer. Take a stroll to the beach, enjoy a round of golf, stock up on supplies at the nearby grocery store, and savor a delicious meal at local restaurants. Whether you're here for work or leisure, our in-law apartment provides a comfortable and convenient base for your stay. We can't wait to welcome you!

Jan 21 – 28

R2,173 ZAR per night

Guesthouse in Portland

5.0 out of 5 average rating, 73 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.

Dec 25 – Jan 1

R2,763 ZAR per night

Guesthouse in Essex

5.0 out of 5 average rating, 27 reviews

Adorable 2 bedroom guesthouse in Essex village

Enjoy the best of both worlds with this remodeled 2 bedroom and 1 bath antique home located on the coveted North Main Street in Essex Village. You are close enough to walk downtown but away from the hustle and bustle. The park-like back yard with an antique trolley bridge and Falls river running through it will give you the perfect place to unwind after a day of activities. Come see why Essex was named “The Perfect Small Town" in the book 1000 Places to See Before You Die!

Dec 10 – 17

R6,201 ZAR per night

Guesthouse in Guilford

5.0 out of 5 average rating, 61 reviews

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.

Jun 11 – 18

R3,947 ZAR per night

Guesthouse in Madison

5.0 out of 5 average rating, 59 reviews

The Barn by the Sound

Spend a weekend in The Barn: a modern designed free-standing building with guest studio apartment above, designed to look like a barn; the studio has views at tree level of a quiet, old neighborhood; one block from Long Island Sound; on a section of the historic old Boston Post Road. There is lots of natural light coming from a large window with a lovely view of a privet hedge on our property overlooking a park like property across the street.

Feb 6 – 13

R3,059 ZAR per night

Guesthouse in East Hampton

4.9 out of 5 average rating, 21 reviews

Family-Friendly Lakeside Cottage

Newly renovated lakeside cottage with stunning views. 2 bedrooms with king beds and a pull out couch, 1.5 bathrooms - 30 second walk to the lake - Fully furnished and equipped - Private rock patio with picnic table and grill - Washer and dryer in unit - Desk for working from home - 2 Kayaks and a paddle board is available for use - Short walk or drive to restaurants, and shops Perfect for romantic getaways or family vacations.

Oct 19 – 26

R6,002 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

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A space thats all yours, with room for everyone

Popular amenities for Middlesex County guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in Groton

4.94 out of 5 average rating, 386 reviews

Quiet studio with sleeping loft and deck

Oct 26 – Nov 2

R2,150 ZAR per night

Guesthouse in Shelter Island

4.97 out of 5 average rating, 105 reviews

Waterfront carriage house studio

Sep 9 – 16

R7,935 ZAR per night

Guesthouse in Southampton

4.95 out of 5 average rating, 411 reviews

Tiny Home in Prime Spot in Southampton Village

Oct 24 – 31

R5,628 ZAR per night

Guesthouse in Jamesport

4.97 out of 5 average rating, 107 reviews

Walk to Beautiful Beach in Heart of Wine Country

Jan 14 – 21

R7,208 ZAR per night

Guesthouse in Mystic

4.78 out of 5 average rating, 90 reviews

Maxson House - a serene and stylish getaway

Oct 13 – 20

R3,992 ZAR per night

Guesthouse in New London

4.98 out of 5 average rating, 97 reviews

Fully Renovated, Ocean Views, Fireplace & Beach

Jan 2 – 9

R5,717 ZAR per night

Guesthouse in Sag Harbor

4.88 out of 5 average rating, 94 reviews

Charming 2BR Cottage, Walk to Town

Feb 23 – Mar 2

R12,710 ZAR per night

Guesthouse in Sprague

4.97 out of 5 average rating, 189 reviews

House on Little River / Writer Retreat

Jan 30 – Feb 6

R2,671 ZAR per night

Guest house rentals with a patio

Guesthouse in Madison

4.95 out of 5 average rating, 56 reviews

The Rising Tide Cottage

Aug 30 – Sep 4

R6,527 ZAR per night

Guesthouse in Norwich

5.0 out of 5 average rating, 25 reviews

Historic Guest Suite

Sep 27 – Oct 4

R2,689 ZAR per night

Guesthouse in Pomfret

5.0 out of 5 average rating, 20 reviews

Cottage in Quiet Corner. Four miles from town.

Nov 5 – 12

R3,749 ZAR per night

Guesthouse in Shelter Island

5.0 out of 5 average rating, 50 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Sep 14 – 21

R7,437 ZAR per night

Guesthouse in Bridgehampton

4.83 out of 5 average rating, 63 reviews

Central Hamptons Guesthouse

Dec 12 – 19

R6,478 ZAR per night

Guesthouse in Hampton Bays

4.91 out of 5 average rating, 43 reviews

Quaint One Bedroom Cottage with Private Entrance

Sep 11 – 18

R6,383 ZAR per night

Guesthouse in Calverton

4.96 out of 5 average rating, 28 reviews

Private Luxe Cottage at Gates of Wine Country

Apr 17 – 24

R9,527 ZAR per night

Guesthouse in Hampton Bays

5.0 out of 5 average rating, 3 reviews

Retro Mid-Century Cottage 1/2 mile to CPI

Oct 28 – Nov 4

R8,375 ZAR per night

Guest house rentals with a washer and dryer

Guesthouse in Glastonbury

4.96 out of 5 average rating, 133 reviews

Unique luxurious private building in historic area

Jul 21 – 28

R2,475 ZAR per night

Guesthouse in New Haven

4.94 out of 5 average rating, 241 reviews

Square 6ix

Oct 11 – 18

R3,625 ZAR per night

Guesthouse in Southold

4.95 out of 5 average rating, 40 reviews

Southold- Adorable 1 Bedroom Cottage

May 9 – 16

R2,577 ZAR per night

Guesthouse in Mystic

5.0 out of 5 average rating, 93 reviews

HERON HOUSE MYSTIC, CT.

Oct 1 – 8

R5,807 ZAR per night

Guesthouse in Southampton

4.88 out of 5 average rating, 43 reviews

Modern Guesthouse

May 31 – Jun 7

R5,279 ZAR per night

Guesthouse in Southampton

4.8 out of 5 average rating, 10 reviews

Southampton Village Getaway

May 15 – 22

R6,703 ZAR per night

Guesthouse in East Quogue

GuestHouse - Tennis court side luxury

May 27 – Jun 3

R8,386 ZAR per night

Guesthouse in Clinton

4.94 out of 5 average rating, 192 reviews

The Gardener's Cottage Dog friendly/ weekly/montly

Oct 23 – 30

R3,524 ZAR per night

Destinations to explore