Prospect Vacation Rentals

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In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Prospect vacation rentals

Terrace/patio
Soothing 2-bedroom lower-level apartment in Berlin

Apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
$246 nightly
The price is $278
Dec 17 - Dec 18
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Smart TV
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$145 nightly
The price is $163
Dec 17 - Dec 18
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Smart TV, fireplace, books, music library
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Apartment in Haddam

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
10.0 out of 10, Exceptional, (27)
"Overall wonderful experience, would highly recommend."
United States
Steven R.
$226 nightly
The price is $256
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Microwave, oven, stovetop, dishwasher
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Apartment in West New Haven

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
2.0 star property
9.4 out of 10, Exceptional, (3)
"Great communication and easy check in, would recommend "
United States
Ethan R.
$115 nightly
The price is $129
Dec 20 - Dec 21
Total with taxes and fees
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Apartment in East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
9.6 out of 10, Exceptional, (10)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
$232 nightly
The price is $240
Dec 22 - Dec 23
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Outdoor dining
Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale

Apartment in East Rock

Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale
9.4 out of 10, Exceptional, (3)
"Great time with friends."
United States
Ianaliz R.
$299 nightly
The price is $339
Dec 17 - Dec 18
Total with taxes and fees
Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale
Interior
The Nest At Elm City Flats.

Apartment in West New Haven

The Nest At Elm City Flats.
9.4 out of 10, Exceptional, (6)
"Nice place! Short but sweet trip. Appreciate how quick your communication was and your accommodations!"
United States
Lori K.
$204 nightly
The price is $232
Dec 17 - Dec 18
Total with taxes and fees
The Nest At Elm City Flats.
Interior
Modern apt in Wooster Square

Apartment in Downtown New Haven

Modern apt in Wooster Square
10.0 out of 10, Exceptional, (2)
"great ty NICE PLACE TO VISIT IN CT"
United States
JOSE
$304 nightly
The price is $304
Dec 17 - Dec 18
Total with taxes and fees
Modern apt in Wooster Square
Interior
Cozy Guest Suite in Historic Home

Vacation Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
$188 nightly
The price is $213
Dec 17 - Dec 18
Total with taxes and fees
Cozy Guest Suite in Historic Home
Exterior
Angelica’s safe haven @ west haven

Apartment in West Haven

Angelica’s safe haven @ west haven
10.0 out of 10, Exceptional, (6)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
$296 nightly
The price is $335
Dec 17 - Dec 18
Total with taxes and fees
Angelica’s safe haven @ west haven
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Vacation Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$271 nightly
The price is $288
Dec 17 - Dec 18
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Interior
Westville Stay • 2BR • Near Yale • Free Parking

Apartment in West New Haven

Westville Stay • 2BR • Near Yale • Free Parking
10.0 out of 10, Exceptional, (3)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
$234 nightly
The price is $234
Jan 12 - Jan 13, 2026
Total with taxes and fees
Westville Stay • 2BR • Near Yale • Free Parking
Desk, iron/ironing board, WiFi, bed sheets
Yale Casa Verde Studio

Apartment in Dwight

Yale Casa Verde Studio
9.6 out of 10, Exceptional, (8)
"Had a great stay!"
United States
Jeffrey C.
$180 nightly
The price is $204
Dec 17 - Dec 18
Total with taxes and fees
Yale Casa Verde Studio
Outdoor dining
Orange Oasis in East Rock |Free Parking| Near Yale and DT|Large Memory Foam Beds

Vacation Home in East Rock

Orange Oasis in East Rock |Free Parking| Near Yale and DT|Large Memory Foam Beds
9.0 out of 10, Wonderful, (8)
"the apartment was so beautiful, clean, and spacious! it was a great area to be in! the beds were SUPER comfortable as well, highlight of my trip!"
United States
milly s.
$332 nightly
The price is $376
Dec 17 - Dec 18
Total with taxes and fees
Orange Oasis in East Rock |Free Parking| Near Yale and DT|Large Memory Foam Beds
Exterior
All New 1BR with tons of Charm

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (6)
"I highly recommend this property!! We were in town for a wedding celebration, and it proved perfect. The property is completely updated, well-appointed and clean. The property is centrally located and close to restaurants, shops and grocery markets. Karl was a great host and communicated with us throughout our stay. I highly recommend!!"
United States
Francis S.
$271 nightly
The price is $288
Dec 20 - Dec 21
Total with taxes and fees
All New 1BR with tons of Charm
Living area
Downtown loft apartment in the heart of downtown New Haven.

Apartment in Downtown New Haven

Downtown loft apartment in the heart of downtown New Haven.
9.4 out of 10, Exceptional, (3)
"The place was so cozy and perfect for a lil getaway so many places nearby!"
United States
Luis R.
$153 nightly
The price is $173
Dec 17 - Dec 18
Total with taxes and fees
Downtown loft apartment in the heart of downtown New Haven.
Fridge, microwave, oven, stovetop
One bedroom apartment in United States of America, New Haven

Apartment in Dwight

One bedroom apartment in United States of America, New Haven
10.0 out of 10, Exceptional, (2)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
$182 nightly
The price is $206
Dec 18 - Dec 19
Total with taxes and fees
One bedroom apartment in United States of America, New Haven
Dining
Stocked home close to Yale, in Heart of New Haven

Vacation Home in Mill River

Stocked home close to Yale, in Heart of New Haven
9.2 out of 10, Wonderful, (18)
"Great value very close to university. "
United States
Lawrence
$195 nightly
The price is $221
Dec 17 - Dec 18
Total with taxes and fees
Stocked home close to Yale, in Heart of New Haven
Interior
Beach Apartment in Woodmont Milford

Apartment in Milford

Beach Apartment in Woodmont Milford
2.0 star property
9.0 out of 10, Wonderful, (2)
"Had a great stay!"
United States
Garry G.
$379 nightly
The price is $429
Dec 17 - Dec 18
Total with taxes and fees
Beach Apartment in Woodmont Milford
Terrace/patio
The Jewel of The Cove - Historic Coastal Retreat

Vacation Home in East Shore

The Jewel of The Cove - Historic Coastal Retreat
2.0 star property
10.0 out of 10, Exceptional, (6)
"loved it so much, beautiful property 100 % would stay again "
United States
Leilani R.
$482 nightly
The price is $513
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Jewel of The Cove - Historic Coastal Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Prospect Hotel Reviews

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Clean room. Great location. Very nice staff."
William 2-night trip
Posted 1 day ago
Holiday Inn Express Southington by IHG

Find out more about Prospect

Everything you need to know about Prospect vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Prospect vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Prospect vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Prospect vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Prospect. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Prospect in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Prospect rentals

At Expedia, we put the best Prospect vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Prospect rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Prospect vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Prospect. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Prospect?

Yes, we have vacation rentals close to top sights in Prospect, or you can go with a more remote option if you'd like a relaxing place to stay. Prospect is known for its golf courses and bars.

What are some of the best vacation home rentals in Prospect?

Private Apartment in Berlin: Visitors like this Prospect vacation home rental. It is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Prospect?

While exploring the area, visit family-friendly sights like Quassy Amusement Park, or get outside and enjoy nature at Beacon Falls Town Recreation Field. In the larger area, you’ll find Palace Theatre and Waterbury City Hall.

What’s a vacation rental in Prospect like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Prospect. Vacation rentals feature extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.