Prospect Vacation Rentals

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Check prices for these dates

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

Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
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.
$236 nightly
The price is $244
Dec 22 - Dec 23
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Smart TV
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
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 22 - Dec 23
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fridge, microwave, oven, stovetop
One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven
Dwight
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.
$183 nightly
The price is $207
Dec 22 - Dec 23
Total with taxes and fees
One bedroom apartment in United States of America, New Haven
Interior
Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking
West New Haven
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.
$235 nightly
The price is $235
Jan 8 - Jan 9, 2026
Total with taxes and fees
Westville Stay • 2BR • Near Yale • Free Parking
Property grounds
#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
$299 nightly
The price is $320
Dec 22 - Dec 23
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
Exterior
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
Downtown New Haven
9.0 out of 10, Wonderful, (12)
"Convenient location. Just off Rte 91. Easy street parking. The studio is as pictured - exposed brick walls, high ceilings. Everything you need for a short stay. "
United States
Lois G.
$176 nightly
The price is $176
Dec 22 - Dec 23
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
Interior
The Nest At Elm City Flats.

The Nest At Elm City Flats.

The Nest At Elm City Flats.
West New Haven
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.
$209 nightly
The price is $237
Dec 22 - Dec 23
Total with taxes and fees
The Nest At Elm City Flats.
Apartment (2 Bedrooms) | Interior
2 Mi to Beach, Shared Yard Space: West Haven Apt!

2 Mi to Beach, Shared Yard Space: West Haven Apt!

2 Mi to Beach, Shared Yard Space: West Haven Apt!
3.0 star property
West Haven
$311 nightly
The price is $358
Dec 22 - Dec 23
Total with taxes and fees
2 Mi to Beach, Shared Yard Space: West Haven Apt!
Exterior
New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury
Southbury
9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$110 nightly
The price is $124
Dec 22 - Dec 23
Total with taxes and fees
New One Bedroom Apartment Centrally Located in Southbury
Exterior
Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west 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
$284 nightly
The price is $322
Dec 22 - Dec 23
Total with taxes and fees
Angelica’s safe haven @ west haven
Fridge, microwave, oven, stovetop
#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
$222 nightly
The price is $239
Jan 5 - Jan 6, 2026
Total with taxes and fees
#26 Beautifully Renovated 2 BR Home
Interior
#31 - Downtown Terryville- 1 Br

#31 - Downtown Terryville- 1 Br

#31 - Downtown Terryville- 1 Br
Plymouth
10.0 out of 10, Exceptional, (1)
"In convenient safe area. Os is easy to contact"
United States
Gina P.
$215 nightly
The price is $230
Dec 22 - Dec 23
Total with taxes and fees
#31 - Downtown Terryville- 1 Br
1 bedroom, iron/ironing board, free WiFi, bed sheets
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Shelton
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
$172 nightly
The price is $195
Dec 22 - Dec 23
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
9.0 out of 10, Wonderful, (8)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$109 nightly
The price is $122
Jan 3 - Jan 4, 2026
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Desk, iron/ironing board, WiFi, bed sheets
Yale Casa Verde Studio

Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.6 out of 10, Exceptional, (8)
"Had a great stay!"
United States
Jeffrey C.
$180 nightly
The price is $204
Dec 22 - Dec 23
Total with taxes and fees
Yale Casa Verde Studio
Dining
Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (69)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
$204 nightly
The price is $231
Dec 27 - Dec 28
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
Exterior
All New 1BR with tons of Charm

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (7)
"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 27 - Dec 28
Total with taxes and fees
All New 1BR with tons of Charm
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
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
Jan 2 - Jan 3, 2026
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
New Britain
10.0 out of 10, Exceptional, (8)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
$218 nightly
The price is $246
Jan 5 - Jan 6, 2026
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Microwave, oven, stovetop, dishwasher
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
2.0 star property
West New Haven
9.4 out of 10, Exceptional, (3)
"Great communication and easy check in, would recommend "
United States
Ethan R.
$125 nightly
The price is $141
Jan 12 - Jan 13, 2026
Total with taxes and fees
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
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

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Great hotel. Really nice reception person. Fast process. Nice room. I recommend fully with 5 stars + . "
Brian 1-night trip
Posted 2 days ago
New Haven Hotel

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 $141 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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: Visitors like this Prospect vacation home rental. It offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

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 Holy Land USA. 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.