Vacation rentals in Orange

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Top-rated vacation rentals in Orange

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Guest favorite

Apartment in Milford

4.94 out of 5 average rating, 107 reviews

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!

Sep 28 – Oct 5

G$42,275 GYD per night

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 508 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Sep 26 – Oct 3

G$41,969 GYD per night

Guest favorite

Bungalow in Milford

4.99 out of 5 average rating, 214 reviews

Spring Sale! Beach Bungalow |WalktoBeach |Pet |Pkg

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.

Nov 5 – 12

G$45,000 GYD per night

Guest favorite

Apartment in Milford

5.0 out of 5 average rating, 48 reviews

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.

Sep 3 – 10

G$35,334 GYD per night

Guest favorite

Loft in Milford

4.94 out of 5 average rating, 95 reviews

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.

Jan 29 – Feb 5

G$26,118 GYD per night

Guest favorite

Home in New Haven

5.0 out of 5 average rating, 169 reviews

Historic New Haven Home

Our family owned New Haven vacation house is a renovated 1920s Tudor. It's located in a quiet, safe, & beautiful neighborhood, close to downtown and Yale. We've carefully preserved historic aspects we love (ie: art deco tile & leaded glass windows), and combined it with central a/c, USB ports, new appliances, gas fireplace, high speed wifi & more. You’re also welcome to use the small screened in porch, patio with chairs, and the yard. The entire house and driveway is yours when you rent.

Apr 24 – May 1

G$31,952 GYD per night

Guest favorite

Guesthouse in Milford

5.0 out of 5 average rating, 32 reviews

The studio downtown

The studio is a new, private, quiet, and peaceful space. It is situated on the second floor of a detached garage with a private entrance. It is located in the historic center of town, within walking distance of the train station, bars, restaurants, and beach. It is ideal for a couple looking for a beach town getaway. The studio has a king-size bed, an eating area, a kitchenette with a fridge, a sink, a double induction cooktop, a seating area, and a bathroom with a rain shower.

Jan 21 – 28

G$27,428 GYD per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

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.

Sep 13 – 20

G$24,139 GYD per night

Guest favorite

Guest suite in Milford

5.0 out of 5 average rating, 14 reviews

Modern Studio & Gamers Paradise Near Downtown

Discover endless fun at our game-filled retreat! Choose from a variety of board games, enjoy a game of bumper pool or darts, and dive into the world of video games. Minutes from Silver Sands Beach, downtown Milford, and main highways, this spacious studio features a workout area, dedicated workspace, full bathroom, kitchenette, and open layout. Perfect for a fun-filled getaway, our home ensures a blend of relaxation and entertainment in a prime location!

Feb 24 – Mar 3

G$25,422 GYD per night

Guest favorite

Guest suite in Shelton

4.81 out of 5 average rating, 264 reviews

Super cozy 1 BR apt. own entrance, great loc.

Very quiet residential neighborhood, very clean, super cozy apartment with two bedrooms, living room; computer desk with work station, kitchenette (no stove), own bathroom, and amenities. 20 minutes away from Bridgeport, 15 minutes away from Yale, New Haven. Lakes in walking distance, Metro-North rail; 7 minutes, local shopping area 1 mile. Bus route in walking distance. Great neighborhood!! All are welcomed. Warm community.

Jan 24 – 31

G$12,972 GYD per night

Superhost

Apartment in Milford

4.89 out of 5 average rating, 207 reviews

Renovated Apartment in a Historic Farmhouse Estate

Take-in fresh air and tranquil views from the 2nd floor deck of a 1-acre property with an adjacent apple orchard. Rustic decor mixes with industrial flair to create an inspiring interior that offers country comforts along with modern amenities. Enjoy hardwood floors, Queen memory foam mattresses, high ceilings, keypad door lock (no keys needed), fast Wifi, central air conditioning, & a private deck. We can't wait to host you!

Nov 15 – 22

G$40,133 GYD per night

Guest favorite

Loft in New Haven

4.92 out of 5 average rating, 279 reviews

969 Dream Loft

Airy and bright, this spacious loft is filled with natural light and stunning upgrades. The loft features high ceilings, sky lights, and thoughtful touches. Special amenities include king size adjustable massaging bed, and a gas fireplace. Kitchen is completely equipped. Washer/dryer available for use on the second floor landing.

May 30 – Jun 6

G$32,421 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Orange vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Orange's top sights

Eisenhower Park10 locals recommend

Whole Foods Market21 locals recommend

Costco Wholesale17 locals recommend

Trader Joe's45 locals recommend

PEZ Visitor Center16 locals recommend

ShopRite of Orange3 locals recommend

Other great vacation rentals in Orange

Guest favorite

Tiny home in Ansonia

5.0 out of 5 average rating, 13 reviews

Cozy Tiny Home for Solo Travelers Near Everything

Jun 12 – 19

G$20,262 GYD per night

Guest favorite

Apartment in Milford

4.95 out of 5 average rating, 75 reviews

Downtown, Private balcony, 1gb fiber Wi-Fi

May 2 – 9

G$31,688 GYD per night

Superhost

Apartment in West Haven

4.85 out of 5 average rating, 27 reviews

Beautiful New Studio Close to Yale!

Jan 20 – 27

G$20,913 GYD per night

Guest favorite

Apartment in Milford

5.0 out of 5 average rating, 8 reviews

Downtown Milford New,Train Access,Pets,Gym,Unit E3

Sep 24 – Oct 1

G$33,977 GYD per night

Guest favorite

Tiny home in Milford

4.96 out of 5 average rating, 53 reviews

Beach Cabana

Oct 13 – 20

G$30,219 GYD per night

Guest favorite

Home in Milford

4.98 out of 5 average rating, 64 reviews

2 Bedroom with sweeping views of Long Island Sound

Oct 6 – 13

G$43,415 GYD per night

Guest favorite

Cottage in Milford

5.0 out of 5 average rating, 63 reviews

Welcome to Ocean’s 55 !

Dec 23 – 30

G$65,829 GYD per night

Guest favorite

Apartment in New Haven

5.0 out of 5 average rating, 29 reviews

Convenient downtown New Haven apartment

Feb 26 – Mar 5

G$23,231 GYD per night

Show all

Quick stats about vacation rentals in Orange

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
240 reviews
Nightly prices starting at
G$4,178 GYD before taxes and fees

Frequently Asked Questions

Do house rentals in Orange have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Orange. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Orange?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with free parking, over 10 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Orange?
Experience the best of Orange with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Orange have free parking?
Absolutely! We offer over 20 house rentals with free parking in Orange. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Orange?
Orange has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Orange have wifi?
Absolutely! We offer over 20 house rentals with wifi in Orange. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Orange have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Orange. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Orange?
Yes! Work meets play with ease at over 10 vacation rentals in Orange featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Orange

Top-rated vacation rentals in Orange

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Orange vacation rentals

Stay near Orange's top sights

Other great vacation rentals in Orange

Tiny home in Ansonia

Apartment in Milford

Apartment in West Haven

Apartment in Milford

Tiny home in Milford

Home in Milford

Cottage in Milford

Apartment in New Haven

Quick stats about vacation rentals in Orange

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Orange have a kitchen?

What are the most popular amenities for House Rentals in Orange?

How much does it cost to stay in house rentals in Orange?

Do house rentals in Orange have free parking?

Are there family-friendly vacation rentals in Orange?

Do house rentals in Orange have wifi?

Do house rentals in Orange have air conditioning?

Are there vacation rentals with a dedicated workspace in Orange?

Destinations to explore