
Holiday rentals in Shelton
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Top-rated holiday rentals in Shelton
Guests agree: these stays are highly rated for location, cleanliness and more.

The Boathouse, private downtown Harborside suite
The Boathouse is a detached one bedroom studio apartment situated behind our home in the heart of Historic downtown Milford. Through a private entrance you will discover a thoughtfully furnished bedroom (queen bed & pull out couch), dining room, full kitchen & bath. It is ideally suited for a couple/small family looking for a memorable beachtown getaway. Walk, rent bikes/kayaks, shop, dine, enjoy art, music, or a day at the beach… our quintessential New England seaside town is sure to charm you!

Private Inn
Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

Charming Guest Cottage with Modern Amenities
Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Bright 1 BR Apt Steps From Yale
Enjoy a bright and cozy 1 bedroom apartment just 2 blocks from the Yale campus and The Shops at Yale. Located in a 3 unit brick building, designated as a property on The National Register of Historic Places, this small renovated 2nd floor apartment maintains the characteristics of the building's original design, while providing all amenities needed for a comfortable stay. Convenient free off street parking provided. Great shops, restaurants, nightlife, and museums can all be accessed by foot.

Fall Sale! Cozy Bungalow/Pet-friendly/Walk2Beach
Welcome to the Beach Bungalow, completely remodeled to the studs in '21! This Woodmont by the Sea home is a 3 block stroll to Anchor Beach & the walkway along beautiful Beach Ave. The home offers a modern kitchen, dining for 6, private back porch & outdoor shower. This +775sf bungalow has a driveway & on-street pkg. It's located in a charming coastal town, walking distance to restaurants, grocery store & Robert Treat Farm and is 2 mi to I95, 10 mi to Yale/New Haven...and mins to breweries.

The Pond Mill Retreat w/ 2 Bdrms & Pool
Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Lovely water front lower-level loft, free parking
This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

Huckleberry Quarters, the Cozy Redding Retreat.
It’s time to book your FALL LEAF-PEEPING sojourn at the Huckleberry Quarters, a beautifully renovated studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy this FALL, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

The River Loft
Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Barn House
Charming, beautiful, spacious farm house originally built in 1773. Meticulously restored and decorated. The perfect getaway for families and friends. Close to downtown Shelton, Bridgeport Ave & Huntington center. This home is breathtaking and on 2 acres of land! Great for exploring, playing, and roasting marshmallows by the fire! The main living room has a wood fire stove which is perfect during the fall and winter. If you’re looking for a relaxing retreat, barn house is for you!

Retreat in New Haven by Stephanie and Damian
Welcome to your retreat in the heart of Westville. This apartment features a spa-like bathroom and a cozy living room with a super-comfy couch and large flatscreen TV. Relax in this centrally located oasis near Yale’s football stadium, Westville Bowl, local art studios, coffee shops, and top restaurants just steps away. Perfect for extended stays, traveling professionals, visiting faculty, or anyone seeking a convenient home base this winter. Discounts for stays of 30+ days.

Peaceful apartment on 3.5 acres w/ Artist studio.
Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.
Popular amenities for Shelton holiday rentals
Other great holiday rentals in Shelton

Beautiful Waterfront on Housatonic River

New & Stylish 2 King Bed Apartment w/ Grand Dining

Cozy studio unit

Beautiful Cozy Apt/ Soaking Tub & Serene Vibes

New & Modern Studio Apartment in Fairfield

Cozy Studio in Bridgeport

Cozy in laws suite in the woods

Renovated 2 bedroom entire apartment w/parking
When is the best time to visit Shelton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 103 | € 93 | € 104 | € 112 | € 112 | € 113 | € 107 | € 106 | € 115 | € 104 | € 103 | € 106 |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
How much does it cost to stay in apartment rentals in Shelton?
Experience the best of Shelton with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Shelton?
Four-legged friends are welcome in Shelton. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Shelton?
Shelton has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Shelton?
Yes! Work meets play with ease at over 30 vacation rentals in Shelton featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Shelton?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with a kitchen, over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Shelton have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Shelton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shelton have free parking?
Absolutely! We offer over 20 house rentals with free parking in Shelton. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Shelton have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Shelton. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Shelton

Total holiday rentals
Explore 60 holiday rentals in Shelton

Nightly prices starting at
Shelton holiday rentals start at € 26 per night before taxes and fees

Verified guest reviews
Over 2,590 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Shelton holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shelton rentals

4.8 Average rating
Shelton stays are highly rated by guests – averaging 4.8 out of 5!
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- Yale University
- Fairfield Beach
- Southampton Beach
- Rye Beach
- Cooper's Beach, Southampton
- Robert Moses State Park
- Thunder Ridge Ski Area
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Bethpage State Park
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- Cedar Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
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- Jennings Beach
- Sandy Beach
- Wildemere Beach
- Kent Falls State Park
- Seaside Beach
- Outer Beach at Smith Point County Park




